US2387587A - Process of manufacturing cyclopentenone derivatives - Google Patents
Process of manufacturing cyclopentenone derivatives Download PDFInfo
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- US2387587A US2387587A US353425A US35342540A US2387587A US 2387587 A US2387587 A US 2387587A US 353425 A US353425 A US 353425A US 35342540 A US35342540 A US 35342540A US 2387587 A US2387587 A US 2387587A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/597—Unsaturated compounds containing a keto groups being part of a ring of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
Definitions
- alkylcyclopentenones from the nitrosochlorides of the alkylcyclopentenes when these are treated with potassium acetate and acetic acid.
- This process is, however, not generally applicable, as the use of dialkylcyclopentenes in which the double bond lies between the substituted nucleuscarbon atoms is not possible.
- the process presupposes, furthermore, the indiflerence of the selected alkyl groups with respect to nitrosylchloride and the like. Besides, the yield is in most cases not satisfying.
- Staudinger and Ruzicka have obtained only about 1 /2 grams of methyl-amyl-cyclopentenone from 318 grams of ethyl-a-bromenanthate and 182 grams of ethyllaevulinate (see also Treif and Werner, Berichte 68, pages 642-643, 1935).
- the C groups excludes the formation of a cyclo 5 (mac 0 CH CH0 0 CHR pentenone nucleus.
- R1 Ra, R3, R4 denote hydrogen or any other desired univalent group, 1. i. methyl, carboxyl or the like.
- R5 is an univalent aliphatic or aromatic or a substituted group.
- condensation agents it is most suitable to the object in view to make use or an aqueous, alcoholic or methyl-alcoholic potassium" hydroxide solution, sodium-hydroxide or barium hydroxide solution, furthermore of a solution 01' alkali-alcoholates, alkaline earth hydroxides, a1- kali-carbonate or alkali-bicarbonate or of a solution of a similar substance, but it is as well possible to employ occasionally aqueous or non-aqueous acids or solutions of acids, salts or the like. Finally, it is possible to carry out the reaction in the gas-phase, the vapor of the dicetone being then subjected to the action of heat, may be with the simultaneous use of dehydrating agents.
- the boiling point of the ketone purified by the semicarbazone is 120-12l.5 at 12 mm.
- the semicarbazone did not show any fusing point depression together with a dihydroj asmonesemicarbazone manufactured according to Duden and Freitag.
- Liquid of B. P.14 1l4-115.
- Semicarbazone: M. P. 230-232 (decomposition)
- Liquid of B. P.11 104.
- the products obtained by the present im-' proved'process are intended for use as perfumes, means for annihilating plant lice and other noxious animals, etc., for the synthesis of curatives, etc., and the like.
- substituted cyclopenteneones which comprises cyclizing diketones oi the iormula CHI-C 0.011-011-0 01mm;
- R1 is a monovalent substituent selected from the group consisting oi hydrogen and methyl
- Ra is selected from the group consisting or hydrogen
- R3 is a radical selected from the group consisting of alkyl, halogenalkyl, carboxyl-alkyl, esterified carboxyl-alkyl, hydroxy-alkyl and ,alkyloxyalkyl, by treating the same with an alkali.
- substituted cyclopentenones which comprises cyclizing diketones of the formula in which R2 is a monovalent substituent selected from the group consisting of hydrogen, methyl and carbonyl and R3 is a radical selected from the group consisting of alkyl, halogen-alkyl, carboxyl-alkyl, esterifled carboxyl-alkyl. hydroxyalkyl and alkyloxy-alkyl by treating the same with an alkali.
- pentenones which comprises cyclizing diketones of the formula oniooonomooomn:
- R1 is a substituent selected from the group consisting of hydrogen and methyl and R3 is a radical selected from the group consisting of alkyl, halogewalkyl, carboxyl alkyl, esterified .carboxyl alkyl, hydroxy-alkyl and alkyloxy-alkyl by treating the same with an alka 4.
- R3 is a radical selected from the group consisting of alkyl, halogewalkyl, carboxyl alkyl, esterified .carboxyl alkyl, hydroxy-alkyl and alkyloxy-alkyl by treating the same with an alka 4.
- R is a radical selected from the group consisting of alkyl, halogen-alkyl, carboxylesterifled carboxyl-alkyl, hydroxy-alkyl and alkyloxy-alkyl by treating the same with an alkali.
- substituted cyclopentenones which comprises cyclizing ,diketones oi the formula cmcocmcmcocmn) in which R. is a carboxyl-alkyl radical. by treating the same with an alkali.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 23,, 1945 PROCESS OF MANUFACTURING CYCLO- PENTENONE DERIVATIVES Heinz Hunsdiecker, Cologne-Braunsfeld, Germany; vested in the Allen Property Custodian No Drawing. Application August 20, 1940, Serial No. 353,425. In Germany January 4, 1939 10 Claims. (Cl. 260-586) The processes having become known up to now for the manufacture of cyclopentenonederivatives can be divided into two groups. In the one thereof the process starts from a finished cyclopentene-nucleus or cyclopentanenucleus respectively. There is thus, obtained for instance, alkylcyclopentenones from the nitrosochlorides of the alkylcyclopentenes when these are treated with potassium acetate and acetic acid. This process is, however, not generally applicable, as the use of dialkylcyclopentenes in which the double bond lies between the substituted nucleuscarbon atoms is not possible. The process presupposes, furthermore, the indiflerence of the selected alkyl groups with respect to nitrosylchloride and the like. Besides, the yield is in most cases not satisfying.
The other of the above mentioned two groups starts from linear compounds. There is, thus, obtained, for instance, methyl-alkyl-cyclopentenones if esters from laevulic acid and esters from a-halogenfatty-acids are used as starting materials (compare, for instance, Helv. Chim. Act. VII, pages 256-257, 1924) Also this process is subjected to similar restrictions as that for the manufacture of alkylcyclopentenones from alkylcyclopentenes. A particularly grave drawback connected therewith in this case is the comparatively slight yield. Thus, Staudinger and Ruzicka have obtained only about 1 /2 grams of methyl-amyl-cyclopentenone from 318 grams of ethyl-a-bromenanthate and 182 grams of ethyllaevulinate (see also Treif and Werner, Berichte 68, pages 642-643, 1935).
o 0011 the C groups excludes the formation of a cyclo 5 (mac 0 CH CH0 0 CHR pentenone nucleus.
I have discovered that, in a surprising contrast to the hitherto usual opinion, the 'y-dicetones are able to form a cyclopentenone nucleus if a methyl-group is in a position adjacent to one of CHs.C O.CH:.CH:.CO.
the two (JO-groups but a methylene-group in a position adjacent to the other of the CO-groups, that is to say, if the 'y-dicetones correspond to the formula In this formula R1, Ra, R3, R4 denote hydrogen or any other desired univalent group, 1. i. methyl, carboxyl or the like. R5 is an univalent aliphatic or aromatic or a substituted group.
The ring closure itself is a very simple operation. In many cases one obtains a practically quantitative yield, if the procedure is carried out CH3 CF:
Thus, cyclopentenonederivatives are obtained when the following compounds are used as starting materials:
(R=methyl, ethyl etc.) OHS-C consents 0 .CHz.CHz.OH:.CH2Br(Cl, J) omcocncmcocnm Ha CHsC O CHzCHC 0 (311211 E: CHaCOCH CHCOCHlR Ha Ha- CHaCO CHzCHCO CHzR etc.
Concerning the condensation agents it is most suitable to the object in view to make use or an aqueous, alcoholic or methyl-alcoholic potassium" hydroxide solution, sodium-hydroxide or barium hydroxide solution, furthermore of a solution 01' alkali-alcoholates, alkaline earth hydroxides, a1- kali-carbonate or alkali-bicarbonate or of a solution of a similar substance, but it is as well possible to employ occasionally aqueous or non-aqueous acids or solutions of acids, salts or the like. Finally, it is possible to carry out the reaction in the gas-phase, the vapor of the dicetone being then subjected to the action of heat, may be with the simultaneous use of dehydrating agents.
The process constituting the present invention is more fully described in detail in the following examples:
First example 5.9 grams oi. 2.5-nonane-dione (B. P.m= 1l2-114) are heated to boiling temperature together with 76 grams of 2%-aqueous sodium hydroxide solution, the mixture being kept at that temperature for several hours. There are obtained 4.15 grams of 3-methyl-2-propylcyclopentene-2-=one-1, which are 80% of the theoretical yield.
B. P.11,5=94,5 Semicarbazone: M. P. 212
, Second example 4.4 grams of 2.5-decandione (B. P.17= 132-134) are heated with 52 grams of 3%- aqueous potassium hydroxide solution to boiling, the mixture being maintained boiling for some time. The oily layer is taken up by means of ethyl ether and is distilled invacuo after the ether has been evaporated. There are obtained 2.9 grams, viz. 74% of the theoretical yield of 3-methyl-2-butyl-cyclopentene-2-one-1 which is a liquid with an agreeable smell.
B. P.12=107 Semicarbazone: M. P.=193-193.5
Third example In a similar manner as in the first and in the second example there are obtained from 9.2 grams undecandione (B. P.14=141, M. P.=33) 7.6 grams, viz. 92% of the theoretical yield of 3-methyl-2-n-amylcyclopentene-2-one-l. This product is dihydrojasmone, as appears from its analysis and its physical constants.
f.: H=10.96 (1:79.28 calc.: H=10.92 :79.45
The boiling point of the ketone purified by the semicarbazone is 120-12l.5 at 12 mm.
The semicarbazone did not show any fusing point depression together with a dihydroj asmonesemicarbazone manufactured according to Duden and Freitag.
Fourth example If 6 grams of 2 methyldecandione-6.9
(B. P.1a=128-l32) are heated together with 65 With higher molecular 'y-dicetones it is recommendable to make use of somewhat stronger condensation agents, an addition of alcohol, more concentrated solutions, solid alkalior a condition, as the success is the same by heating for a longer period with dilute solutions.
Fifth example 2.2 grams of 2.5-dodecandione (B. P.1z== 148 M. P.=39.5-40.5, semioarbazone: M. P'.= 187) are stirred with 11 grams of hot 3%-potassium hydroxide solution for several days. After cooling and extracting with ethyl-ether there are obtained 1.6 grams, viz. of the theoretical yield, of 3-methyl-2-hexylcyclopentene-2-one-1.
B. P.1s=142-144 Semicarbazone: M. P.=l63.5-l64.5'
Sixth example A mixture oi. 3.6 grams of 2.5-tetradecandione' (M. P.=50-51), 20 com. of a 10%-potassium hydroxide solution and 30 ccm. of alcohol is heated to boiling and maintained at this temperature for 2 hours, whereaiter the alcohol is distilled-oil and the oily layer is taken up by ethyl-ether. Yield: 2.7 grams of 3-methyl-2-octylcyclopentene-Z-one-l, which are 81.4% of the theoretical yield.
Liquid of floweryodour; B. P.1:=157-160 Semicarbazone: M. P.=159-159.5
Seventh example A solution of 4.9 grams of 2.5-octadecandione (M. P.=70.5) in 30 ccm. of alcohol is heated to boiling together with 20 com. of a 50%-aqueous potassium hydroxide solution, this temperature being maintained for 1 hour. There are obtained 3.1 grams of 3-methyl-2-dodecylcyclopentene-Z-one-l, which are 66% of thetheoretical yield.
M. P.=34-'i5.5 B. P.2.5=171-173 Semicarbazone: M. P.=15l.5-152.5
Eighth example When ll-methoxy-2.5-undecandione is heated with a mixture of 40 com. of a 5%-aqueous sodium hydroxide solution and 10 com. of alcohol 3 methyl- 2- (e-methoxyamyl) -cyclopentene-2- one-l is obtained.
B. P.i4=146-148 Semicarbazone; M. P.=l50-150.5
Ninth example 11.5 grams of 7-methyl-4.7-diketoheptoic acid (M. P.=76-'78) are dissolved in 200 ccm. of potassium hydroxide solution, the mixture being then heated to boiling for 2 hours. The originally colorless solution becomes somewhat darker. The mixture is cooled and neutralised with an amount of sulphuric acid accurately equivalent t the amount of the potassium hydroxide solution. Then the aqueous solution is concentrated by evaporation and the residueis extracted with ethyl-acetate. After the ethylacetate has evaporated there are obtained 10 grams instead of, theoretically, 10.3 grams of 3- methyl cyclopentene 2 one-1-acetic-acid-2. After the recrystallisation of this product from ethyl acetate this acid forms stout Crystals of M. P.=108.5-110.5 Semicarbazone: M. P.=2l3.5-216 (decomposition) Tenth example From 11 methyl 4,7 diketoundecanoic acid steamer M. 12:63-65. Equivalent weight=212 instead of 210 Eleventh example The condensation product of sodium salt of propionyl-acetic-acid-ester and bromoacetone is heated for some time together with an excess of 2%sodium solution. The ester forms the corresponding y-dicetone and this reacts by ring closure similarly to that described in the preceding example. There is obtained 2,3'-dimethylcyclo-pentene-2-one-l.
Liquid of B. P.1e=7578 Semicarbazone: M. P.=247.5 (decomposition) Twelfth example 25 grams of a-capronyl-laevulic acid-ethylester are gradually heated with 1 liter of 2% sodium iwdroxide solution to boiling, neutralised after a short period of boiling and then extracted with ethyl-ether. There are obtained 10.7 grams, equal to 73.3% of the theoretical yield,.of 3- methyl-2-butylcyclopentene-2-one-1 of B. P.m=102-107 Semicarbazone: M. P.=192
Thirteenth example In correspondence with the description concerning the preceding example 42.5 grams of a-heptene-(4)-oyl-laevulic acid-ethyl-ester are heated together with a 2%-sodium hydroxide solution to boiling. A sufllcient quantity of acid is added and the product extracted with ethylether. There are obtained 17.6 grams=65% of the theoretical yield of 3-methyl-2-(penten-2- yl)-cyc1opentene-2-0ne-1. B. P.e=122. The
product is identical with the natural lasmone.
In a similar manner it has been possible to obtain the corresponding hexylcyclopentenonederivates from the a-enanthoyland the a-caprylyl-laevulic acid ethyl-ester.
Fourteenth example 25 grams of a-capronyl-p-methyl-laevulic acidethyl-ester have been treated in the manner described in the twelfth example. There has been obtaind the 3Z4-dimethyl-2-butylcyclopentene-2- one-1.
Liquid of B. P.14=1l4-115. Semicarbazone: M. P.=230-232 (decomposition) There have, furthermore, been obtained from a-caprony1--methyl-1aevulic acid ethyl ester the 3.5 dimethyl-2-butylcyc1opentene-2-one-l. Liquid of B. P.11=104.
Fifteenth example Sixteenth example 2.5-undecandione is slowly distilled over sillcagel containing a little alkalihydroxide and Seventeenth example A mixture of 50 grams of cold saturated p0- tassium-carbonate solution, 30 com. of alcohol and 4 grams of 2.5-dodecandione is heated under shaking in a sealed tube for at least one day to to 140". After settling of the process there are obtained about 80%, of the theoretical yield of 3-methyl-2-hexylcyclopentene-2-one-1.
Eighteenth example 4 grams of dodecandione are dissolved in 50 com. of n methyl-alcoholic barium hydroxide solution and are kept boiling for 2 or 3 hours. There is obtained a yield of 64% of 3-:methy1-2- hexylcyclopentene-2-one-1.
B. P.1e=-137 Nineteenth example 2 grams of sodium metal are dissolved in 40 grams of anhydrous methanol, whereaiter 17 grams of acetic ester and 4 grams of dodecandione are added. The acetic ester is partially saponificated by the water split off during the reaction. In this case sodium methylate is the condensation agent. There are obtained 2.8 grams, viz. 77% oi the theoretical yield, of 3- methyl-2-hexylcyclopentene-2-one-1.
The products obtained by the present im-' proved'process are intended for use as perfumes, means for annihilating plant lice and other noxious animals, etc., for the synthesis of curatives, etc., and the like.
I claim:
1. The process of making substituted cyclopenteneones which comprises cyclizing diketones oi the iormula CHI-C 0.011-011-0 01mm;
in which R1 is a monovalent substituent selected from the group consisting oi hydrogen and methyl, Ra is selected from the group consisting or hydrogen, methyl and carboxyl and R3 is a radical selected from the group consisting of alkyl, halogenalkyl, carboxyl-alkyl, esterified carboxyl-alkyl, hydroxy-alkyl and ,alkyloxyalkyl, by treating the same with an alkali.
2. The process of making substituted cyclopentenones which comprises cyclizing diketones of the formula in which R2 is a monovalent substituent selected from the group consisting of hydrogen, methyl and carbonyl and R3 is a radical selected from the group consisting of alkyl, halogen-alkyl, carboxyl-alkyl, esterifled carboxyl-alkyl. hydroxyalkyl and alkyloxy-alkyl by treating the same with an alkali.
3. The process of substituted cycloalkyl,
pentenones which comprises cyclizing diketones of the formula oniooonomooomn:
in which R1 is a substituent selected from the group consisting of hydrogen and methyl and R3 is a radical selected from the group consisting of alkyl, halogewalkyl, carboxyl alkyl, esterified .carboxyl alkyl, hydroxy-alkyl and alkyloxy-alkyl by treating the same with an alka 4. The process of 'making substituted cyclopentenones which comprises cyclizing diketones oi the formula.
CHa.CO.CI-I2.CH2.CO.CH2R3 c in which R: is a radical selected from the group consisting of alkyl, halogen-alkyl, carboxylesterifled carboxyl-alkyl, hydroxy-alkyl and alkyloxy-alkyl by treating the same with an alkali.
5. The process of making substituted cyclopentenones which comprises cyclizlng diketones ot the formula omcocmcmcoomn in which R. is an alhrl radical, by treating the same with an alkali.
6. The process of making substituted cyclopentenones which comprises cyclizing ,diketones oi the formula cmcocmcmcocmn) in which R. is a carboxyl-alkyl radical. by treating the same with an alkali.
7. The process which comprises cyclizing 7- methyl-4,'l-'diketoheptoic acid, by treating the I same with an alkali.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2387587X | 1939-01-04 |
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| US2387587A true US2387587A (en) | 1945-10-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| US353425A Expired - Lifetime US2387587A (en) | 1939-01-04 | 1940-08-20 | Process of manufacturing cyclopentenone derivatives |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526171A (en) * | 1946-09-02 | 1950-10-17 | Firmenich & Co | Preparation of beta-methyl-cyclopentadecanone |
| US2574500A (en) * | 1950-05-11 | 1951-11-13 | Milton S Schechter | Hydroxydiketones |
| US2623071A (en) * | 1948-05-13 | 1952-12-23 | Synor Res Lab Inc | Preparation of substituted cyclopentenones |
| US2661374A (en) * | 1949-02-08 | 1953-12-01 | Milton S Schechter | Synthesis of 4-hydroxy-2-cyclo-penten-1-ones |
| US2671808A (en) * | 1951-06-23 | 1954-03-09 | Merck & Co Inc | Processes for preparing polycyclic alpha, beta-unsaturated ketones |
| US2717262A (en) * | 1949-08-15 | 1955-09-06 | Chemical Elaborations Inc | Process of producing chrysanthemic acid esters of cyclopentenyl ketonic alcohols and products |
| DE1146877B (en) * | 1960-06-11 | 1963-04-11 | Hoechst Ag | Process for the preparation of 3'-keto -? - cyclopenteno (1 ', 2': 16, 17) derivatives of the androstene and 5ª ‰ -androstane series |
| US3124615A (en) * | 1964-03-10 | Carotenoid compounds | ||
| US3215712A (en) * | 1957-01-18 | 1965-11-02 | Union Carbide Corp | Process for the production of cyclic organic compounds |
| US3287372A (en) * | 1964-07-09 | 1966-11-22 | Eastman Kodak Co | Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones |
| US3907896A (en) * | 1972-04-07 | 1975-09-23 | Givaudan Corp | Process for preparation of cyclopentenones |
| US3981891A (en) * | 1972-01-18 | 1976-09-21 | Societe Anonyme Roure Bertrand Dupont | Cyclopentanone derivatives, odoriferous compositions containing them and process of preparation thereof |
| US4111992A (en) * | 1976-09-15 | 1978-09-05 | Hoffmann-La Roche Inc. | Preparation of food coloring agents |
| US4384144A (en) * | 1976-04-05 | 1983-05-17 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing cyclopentenone derivatives |
| US4463194A (en) * | 1982-02-26 | 1984-07-31 | Scm Corporation | Process for making piperitone from plinols |
| WO1987003287A2 (en) * | 1985-11-20 | 1987-06-04 | L. Givaudan & Cie Societe Anonyme | PROCESS FOR PREPARING alpha-HYDROXY CARBONYL COMPOUNDS |
| EP0621253A2 (en) † | 1993-02-11 | 1994-10-26 | Albemarle Corporation | Process for preparing cyclopentenones |
-
1940
- 1940-08-20 US US353425A patent/US2387587A/en not_active Expired - Lifetime
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124615A (en) * | 1964-03-10 | Carotenoid compounds | ||
| US2526171A (en) * | 1946-09-02 | 1950-10-17 | Firmenich & Co | Preparation of beta-methyl-cyclopentadecanone |
| US2623071A (en) * | 1948-05-13 | 1952-12-23 | Synor Res Lab Inc | Preparation of substituted cyclopentenones |
| US2661374A (en) * | 1949-02-08 | 1953-12-01 | Milton S Schechter | Synthesis of 4-hydroxy-2-cyclo-penten-1-ones |
| US2717262A (en) * | 1949-08-15 | 1955-09-06 | Chemical Elaborations Inc | Process of producing chrysanthemic acid esters of cyclopentenyl ketonic alcohols and products |
| US2574500A (en) * | 1950-05-11 | 1951-11-13 | Milton S Schechter | Hydroxydiketones |
| US2671808A (en) * | 1951-06-23 | 1954-03-09 | Merck & Co Inc | Processes for preparing polycyclic alpha, beta-unsaturated ketones |
| US3215712A (en) * | 1957-01-18 | 1965-11-02 | Union Carbide Corp | Process for the production of cyclic organic compounds |
| DE1146877B (en) * | 1960-06-11 | 1963-04-11 | Hoechst Ag | Process for the preparation of 3'-keto -? - cyclopenteno (1 ', 2': 16, 17) derivatives of the androstene and 5ª ‰ -androstane series |
| US3287372A (en) * | 1964-07-09 | 1966-11-22 | Eastman Kodak Co | Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones |
| US3981891A (en) * | 1972-01-18 | 1976-09-21 | Societe Anonyme Roure Bertrand Dupont | Cyclopentanone derivatives, odoriferous compositions containing them and process of preparation thereof |
| US3907896A (en) * | 1972-04-07 | 1975-09-23 | Givaudan Corp | Process for preparation of cyclopentenones |
| US4384144A (en) * | 1976-04-05 | 1983-05-17 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing cyclopentenone derivatives |
| US4111992A (en) * | 1976-09-15 | 1978-09-05 | Hoffmann-La Roche Inc. | Preparation of food coloring agents |
| US4463194A (en) * | 1982-02-26 | 1984-07-31 | Scm Corporation | Process for making piperitone from plinols |
| WO1987003287A2 (en) * | 1985-11-20 | 1987-06-04 | L. Givaudan & Cie Societe Anonyme | PROCESS FOR PREPARING alpha-HYDROXY CARBONYL COMPOUNDS |
| WO1987003287A3 (en) * | 1985-11-20 | 1987-08-13 | Givaudan & Cie Sa | Process for preparing alpha-hydroxy carbonyl compounds |
| US4892966A (en) * | 1985-11-20 | 1990-01-09 | Givaudan Corporation | Acetoacetic acid ester derivatives for the manufacture of α-hydroxycarbonyl compounds |
| EP0621253A2 (en) † | 1993-02-11 | 1994-10-26 | Albemarle Corporation | Process for preparing cyclopentenones |
| EP0621253B2 (en) † | 1993-02-11 | 2000-08-09 | Albemarle Corporation | Process for preparing cyclopentenones |
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