EP0000771B1 - 2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes - Google Patents
2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes Download PDFInfo
- Publication number
- EP0000771B1 EP0000771B1 EP19780100580 EP78100580A EP0000771B1 EP 0000771 B1 EP0000771 B1 EP 0000771B1 EP 19780100580 EP19780100580 EP 19780100580 EP 78100580 A EP78100580 A EP 78100580A EP 0000771 B1 EP0000771 B1 EP 0000771B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dimethyl
- olfactory
- preparation
- methyl
- trimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 57
- 238000000034 method Methods 0.000 title claims description 8
- DUKMHUVJUINORY-UHFFFAOYSA-N 2,5,7-trimethyloctan-3-ol Chemical compound CC(C)CC(C)CC(O)C(C)C DUKMHUVJUINORY-UHFFFAOYSA-N 0.000 title description 15
- HDQVGGOVPFQTRB-UHFFFAOYSA-N 6,8-dimethylnonan-2-ol Chemical compound CC(C)CC(C)CCCC(C)O HDQVGGOVPFQTRB-UHFFFAOYSA-N 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 4
- -1 1-hydroxy-2-methyl-propyl residue Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003205 fragrance Substances 0.000 claims description 11
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 7
- VWLITJGXNSANSN-UHFFFAOYSA-N 3,5-dimethylhexanal Chemical compound CC(C)CC(C)CC=O VWLITJGXNSANSN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VCTQUEJJWZLVMW-UHFFFAOYSA-N 2,5,7-trimethylocta-1,4-dien-3-one Chemical compound CC(C)CC(C)=CC(=O)C(C)=C VCTQUEJJWZLVMW-UHFFFAOYSA-N 0.000 claims description 5
- RUVLMXDRMVWJMQ-UHFFFAOYSA-N 2,5,7-trimethyloctan-3-one Chemical compound CC(C)CC(C)CC(=O)C(C)C RUVLMXDRMVWJMQ-UHFFFAOYSA-N 0.000 claims description 4
- UEHONTCNOHEQEF-YLNKAEQOSA-N (3e,5e)-6,8-dimethylnona-3,5-dien-2-one Chemical compound CC(C)C\C(C)=C\C=C\C(C)=O UEHONTCNOHEQEF-YLNKAEQOSA-N 0.000 claims description 3
- ZMSJESOBNLWMBZ-UHFFFAOYSA-N 6,8-dimethylnon-3-en-2-ol Chemical compound CC(C)CC(C)CC=CC(C)O ZMSJESOBNLWMBZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- QDUPSZDGKOSGHY-UHFFFAOYSA-N 2,5,7-trimethyloct-4-en-3-ol Chemical compound CC(C)CC(C)=CC(O)C(C)C QDUPSZDGKOSGHY-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 14
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
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- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 4
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- 240000005385 Jasminum sambac Species 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
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- 150000002576 ketones Chemical class 0.000 description 4
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- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 description 3
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 3
- UIDQUMSWIAGPLW-UHFFFAOYSA-N 4-hydroxy-6,8-dimethylnonan-2-one Chemical compound CC(C)CC(C)CC(O)CC(C)=O UIDQUMSWIAGPLW-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CIXAYNMKFFQEFU-UHFFFAOYSA-N (4-Methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
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- XJHRZBIBSSVCEL-ARJAWSKDSA-N (Z)-non-6-en-1-ol Chemical compound CC\C=C/CCCCCO XJHRZBIBSSVCEL-ARJAWSKDSA-N 0.000 description 2
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- IWHOGRSAWLWEAW-UHFFFAOYSA-N 2,4,7-trimethyloct-7-en-5-yn-4-ol Chemical compound CC(C)CC(C)(O)C#CC(C)=C IWHOGRSAWLWEAW-UHFFFAOYSA-N 0.000 description 2
- OVOVDHYEOQJKMD-UHFFFAOYSA-N 2,4-dimethylpentan-1-ol Chemical compound CC(C)CC(C)CO OVOVDHYEOQJKMD-UHFFFAOYSA-N 0.000 description 2
- 229940029225 2,6-dimethyl-5-heptenal Drugs 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
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- 238000003747 Grignard reaction Methods 0.000 description 1
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- WHIJSULEEDNKPD-UHFFFAOYSA-N Linalyl anthranilate Chemical compound CC(C)=CCCC(C)(C=C)OC(=O)C1=CC=CC=C1N WHIJSULEEDNKPD-UHFFFAOYSA-N 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 244000052585 Rosa centifolia Species 0.000 description 1
- 235000016588 Rosa centifolia Nutrition 0.000 description 1
- 244000181025 Rosa gallica Species 0.000 description 1
- 235000000533 Rosa gallica Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000001399 angelica archangelica l. seed absolute Substances 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XOYYHTTVCNEROD-UHFFFAOYSA-N hex-1-enyl 2-hydroxybenzoate Chemical compound CCCCC=COC(=O)C1=CC=CC=C1O XOYYHTTVCNEROD-UHFFFAOYSA-N 0.000 description 1
- YDZCHDQXPLJVBG-UHFFFAOYSA-N hex-1-enyl acetate Chemical compound CCCCC=COC(C)=O YDZCHDQXPLJVBG-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000001735 hyssopus officinalis l. herb oil Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- CBVWMGCJNPPAAR-UHFFFAOYSA-N n-(5-methylheptan-3-ylidene)hydroxylamine Chemical compound CCC(C)CC(CC)=NO CBVWMGCJNPPAAR-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JETNPTUJXPNCAS-UHFFFAOYSA-N nona-3,5-dien-2-one Chemical compound CCCC=CC=CC(C)=O JETNPTUJXPNCAS-UHFFFAOYSA-N 0.000 description 1
- IWPOSDLLFZKGOW-UHFFFAOYSA-N oct-3-enoic acid Chemical compound CCCCC=CCC(O)=O IWPOSDLLFZKGOW-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- GTVITUZSWANKRK-UHFFFAOYSA-N propan-2-yloxycyclododecane Chemical compound CC(C)OC1CCCCCCCCCCC1 GTVITUZSWANKRK-UHFFFAOYSA-N 0.000 description 1
- 125000003186 propargylic group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
Definitions
- the invention relates to new fragrances, namely compounds of the formula wherein R represents the 1-hydroxy-2-methyl-propyl or the 3-hydroxy-butyl radical.
- Formula I accordingly comprises 2,5,7-trimethyloctan-3-01 (la) and 2,4-dimethyl-nonan-8-ol (Ib).
- Chloride, bromide and iodide are suitable as halide; bromide and chloride are particularly suitable.
- Raney nickel and palladium are expediently suitable as catalysts.
- the octanone can also be reduced to alcohol using sodium borohydride or lithium aluminum hydride (L.F. Fieser & M. Fieser, Reagents for Organic Synthesis, John Wiley & Sons 1967, 582, 1049).
- 1,4-octadienone it is expedient first to work at room temperature in order first to hydrogenate the double bonds, and then - for the purpose of hydrogenating the keto group - at elevated temperature.
- This latter hydrogenation can e.g. at temperatures of 120-150 ° C, especially at about 140 ° C.
- nonenol it is preferred to start with material prepared in situ, which is accessible, for example, by catalytic hydrogenation from 6,8-dimethyl-3-nonen-2-one using copper chromite.
- the 3,5-nonadienone is also preferably hydrogenated using copper chromite.
- the nonanone is expediently reduced to the alcohol Ib using sodium borohydride or lithium aluminum hydride.
- the 2,4-dimethylpentyl halides required for process variant a) can be obtained by adding hydrogen halide to 2,4-dimethyl-1-pentene according to methods known per se - in the presence of a peroxide - or by replacing the primary alcoholic grouping of 2,4- Dimethylpentanol - also in a manner known per se by means of phosphorus halides - accessible.
- 2,5,7-trimethyl-1,4-octadien-3-one is known, for example, from 2,4,7-trimethyl-7-octen-5-yn-4-ol by propargylic rearrangement Way with the help of a vanadium catalyst - possible.
- Catalytic hydrogenation of the dienone obtained at room temperature - as described above - makes 2,5,7-trimethyl-3-octane p n accessible.
- the 6,8-dimethyl-3-nonen-2-one is accessible, for example, by aldol condensation of 3,5-dimethylhexanal with acetone.
- the alcohols I have special organoleptic properties which make them particularly suitable as fragrances.
- the invention accordingly also relates to the use of I, in particular in the form of mixtures, as fragrances, and fragrance compositions which are characterized by a content of these alcohols I.
- the compound la used as a fragrance according to the invention is distinguished by interesting fruity (apricot-like) smell nuances.
- the alcohol Ib on the other hand, is characterized by a pleasantly floral, fruity, earthy green, mushroom note, whereby aldehydic secondary notes can be identified.
- the compounds can accordingly serve, for example, for perfuming products such as cosmetics (soaps, mouthwashes, deodorants, shampoos, lotions, ointments, powders, etc.), detergents, etc., the compounds preferably not alone, but in the form of compositions other fragrances are used.
- 2,5,7-trimethyi-octan-3-oi produces a velvety, rounded effect in bouquets of various directions, which can be much more important than the apricot-like odor.
- 2,4, -dimethyl-nonan-8-ol which has an earthy, natural note, its addition in compositions achieves considerable reinforcement and a radiance that is particularly noticeable in rose and jasmine notes. Since the new compounds are also saturated alcohols, they are extremely stable in mixtures.
- Compounds I are suitable as fragrances because of their high harmonic insertion capacity, in particular in combination with a number of natural fragrances, e.g. Galbanum oil, vetiver oil, patchouli oil, cedarwood oil, bergamot oil, spruce needle oil, petitgrain oil, tree moss, lemon oil, coriander oil, angelica seed oil, cardamom oil.
- natural fragrances e.g. Galbanum oil, vetiver oil, patchouli oil, cedarwood oil, bergamot oil, spruce needle oil, petitgrain oil, tree moss, lemon oil, coriander oil, angelica seed oil, cardamom oil.
- Compound la can also be used advantageously in mixtures with mastic oil, palmarosa oil, jasmine absolute, mandarin oil and hyssop oil, while compound Ib, on the other hand, produces desired effects with ylang-ylang oil.
- the compounds Ia and Ib can accordingly be used in the production of compositions and - as the production above shows - using a wide range of known odoriferous substances, in particular for the production of compositions with fruity, floral, green, woody, chyper-like and cologne-like notes.
- Alcohol Ib has a natural, mushroom-like odor that is reminiscent of damp forests. Because of this property, Ib, for example in jasmine or rose compositions, significantly enhances the desired natural character of the perfume. The radiance that the compound Ib gives to compositions is particularly valuable in the production of Compositions used in industrial perfumery, such as perfuming soaps and washing powders.
- the concentration of the compounds I can vary within wide limits, for example between about 0.01 (detergents) and about 15% by weight (alcoholic solutions).
- concentrations can of course also be higher.
- the perfume bases can be used in the usual way for perfuming Eaux de Cologne, Eaux de toilette, lotions, creams, shampoos, soaps and detergents, etc.
- n D 20 1.4736
- 64 g of the ketone are hydrogenated in a stirred autoclave in the presence of 6 g of copper chromite under a hydrogen pressure of 40 bar.
- the temperature is first brought to 140 ° C.
- the hydrogen absorption ceases (after 3 hours)
- the mixture is heated to 170 ° C. and kept between 165 and 170 ° C. for 3 hours.
- the catalyst is filtered off with suction and distilled.
- 65 g of chemically pure 2,4-dimethyl-nonan-8-ol are obtained (yield: 85.4%).
- This composition probably has the character of a lily of the valley and targets lilac; for the time being, however, it appears synthetic and somewhat aggressive. After adding 100 parts by weight of 2,5,7-trimethyl-octan-3-ol there is a velvety impression, the note now appears rounded and fruity.
- this composition has a fruity character; the addition of 2,5,7-trimethyloctan-3-ol strengthens and improves the fruity note in the direction of apricots, the natural effect of ripe apricots is achieved.
- the 100 parts by weight of 2,5,7-trimethyloctan-3-ol impart a natural, rounded character to the mixture, the typical note of the ripe melon is more recognizable.
- This floral base is particularly suitable for perfuming soaps and washing powders. With a dosage of 1 to 1.5% by weight in soaps, the composition behaves like an extremely stable, powerful perfume. In washing powders, the optimal effect is obtained at a dosage of 0.1 to 0.3%; the floral note is particularly emphasized by the presence of 2,4-dimethyl-nonan-8-ol.
- This composition represents an "ordinary" rose composition. If you now add 145 parts by weight of 2,4-dimethyl-nonan-8-ol, you get a base with much more volume, which looks more natural and especially on rose petals and on the "Rose de mai "(cross between Rosa centifolia and Rosa gallica).
- This classic chypre base is clearly improved by adding 100 parts by weight of 2,4-dimethyl-nonan-8-ol, creating a floral and green shade and enhancing the (desired) smell of undergrowth.
- the conventional lilac composition gets an earthy shade, which makes the otherwise “synthetic" smell more balanced, flowery, more natural.
- the new alcohol has a rounded effect.
- the composition with the new alcohol appears less “sharp”, but more powerful, it is much more suitable for perfumery.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Claims (3)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU77923A LU77923A1 (de) | 1977-08-04 | 1977-08-04 | Verfahren zur herstellung eines neuen riechstoffes |
LU77923 | 1977-08-04 | ||
CH6537/78 | 1978-06-15 | ||
CH653778 | 1978-06-15 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0000771A2 EP0000771A2 (fr) | 1979-02-21 |
EP0000771A3 EP0000771A3 (en) | 1979-06-27 |
EP0000771B1 true EP0000771B1 (fr) | 1981-09-16 |
Family
ID=25699733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19780100580 Expired EP0000771B1 (fr) | 1977-08-04 | 1978-08-02 | 2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes |
Country Status (7)
Country | Link |
---|---|
US (1) | US4198532A (fr) |
EP (1) | EP0000771B1 (fr) |
JP (1) | JPS5427506A (fr) |
DE (2) | DE2833885A1 (fr) |
FR (1) | FR2399240A1 (fr) |
GB (1) | GB2001984B (fr) |
NL (1) | NL7808230A (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6058209B2 (ja) * | 1978-12-01 | 1985-12-19 | エーザイ株式会社 | β,γ−ジヒドロポリプレニルアルコ−ルおよびそれからなる血圧降下剤 |
ATE14489T1 (de) * | 1980-03-13 | 1985-08-15 | Square D Starkstrom Gmbh | Elektromagnetisches schuetz. |
US4532361A (en) * | 1980-06-19 | 1985-07-30 | International Flavors & Fragrances Inc. | Methyl substituted-2-oxohexane derivatives and processes for preparing and using same |
US4335009A (en) * | 1980-06-19 | 1982-06-15 | International Flavors & Fragrances Inc. | Mixture of aliphatic C10 branched olefin epoxides and use thereof in augmenting or enhancing the aroma of perfumes and/or articles |
US4420423A (en) * | 1980-10-09 | 1983-12-13 | International Flavors & Fragrances Inc. | Methyl substituted-2-oxohexane derivatives and process for preparing and using same |
US4421679A (en) * | 1980-10-09 | 1983-12-20 | International Flavors & Fragrances Inc. | Methyl substituted-2-oxohexane derivatives and processes for preparing and using same |
US4406810A (en) * | 1981-07-06 | 1983-09-27 | International Flavors & Fragrances Inc. | Use of Prins reaction products of diisobutylene in augmenting or enhancing the aroma of detergents |
GB0916363D0 (en) * | 2009-09-18 | 2009-10-28 | Givaudan Sa | Organic compounds |
ES2653942T3 (es) | 2012-06-01 | 2018-02-09 | Kao Corporation | Composición de perfume |
JP5709969B1 (ja) | 2013-11-29 | 2015-04-30 | 花王株式会社 | 香料組成物 |
MX2020012843A (es) * | 2018-05-31 | 2021-02-18 | S H Kelkar & Company Ltd | Alcoholes secundarios aromatizantes y sus composiciones. |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2838576A (en) * | 1958-06-10 | Tertiary alcohols | ||
US3125605A (en) * | 1964-03-17 | Process for the production of alcohols | ||
US3308172A (en) * | 1962-08-22 | 1967-03-07 | Koppers Co Inc | Asymmetric synthesis of alcohols |
US3910897A (en) * | 1972-04-21 | 1975-10-07 | Hoffmann La Roche | Pest retardants |
US3833635A (en) * | 1972-06-23 | 1974-09-03 | Zoecon Corp | 2,4-diene thiolesters and acids |
CH583672A5 (fr) * | 1974-03-15 | 1977-01-14 | Givaudan & Cie Sa | |
NL7602686A (nl) * | 1976-03-15 | 1977-09-19 | Naarden International Nv | Werkwijze ter bereiding van parfumcomposities ter bereiding van als parfumgrondstof bruikbare nieuwe alkadieenderivaten alsmede geparfumeerde voorwer- pen. |
-
1978
- 1978-07-25 US US05/927,809 patent/US4198532A/en not_active Expired - Lifetime
- 1978-08-02 FR FR7822835A patent/FR2399240A1/fr active Pending
- 1978-08-02 EP EP19780100580 patent/EP0000771B1/fr not_active Expired
- 1978-08-02 DE DE19782833885 patent/DE2833885A1/de not_active Withdrawn
- 1978-08-02 DE DE7878100580T patent/DE2861081D1/de not_active Expired
- 1978-08-03 GB GB7832132A patent/GB2001984B/en not_active Expired
- 1978-08-03 JP JP9417178A patent/JPS5427506A/ja active Granted
- 1978-08-04 NL NL7808230A patent/NL7808230A/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
GB2001984B (en) | 1982-01-27 |
JPS636532B2 (fr) | 1988-02-10 |
FR2399240A1 (fr) | 1979-03-02 |
DE2861081D1 (en) | 1981-12-03 |
EP0000771A3 (en) | 1979-06-27 |
NL7808230A (nl) | 1979-02-06 |
GB2001984A (en) | 1979-02-14 |
JPS5427506A (en) | 1979-03-01 |
US4198532A (en) | 1980-04-15 |
DE2833885A1 (de) | 1979-02-15 |
EP0000771A2 (fr) | 1979-02-21 |
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