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CH133680A - Process for the preparation of 1-Ox0-2-methyl-3-p-isopropyl-phenyl-propene-2. - Google Patents

Process for the preparation of 1-Ox0-2-methyl-3-p-isopropyl-phenyl-propene-2.

Info

Publication number
CH133680A
CH133680A CH133680DA CH133680A CH 133680 A CH133680 A CH 133680A CH 133680D A CH133680D A CH 133680DA CH 133680 A CH133680 A CH 133680A
Authority
CH
Switzerland
Prior art keywords
isopropyl
propene
methyl
phenyl
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH133680A publication Critical patent/CH133680A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
    • 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
    • C07C45/74—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 combined with dehydration

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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

  

  Verfahren zur     Darstellung    von     1-Oxo-2-inetliyl-3-p-isopropyl-phenyl-propen-2.            Crem:iss    dein Verfahren des Hauptpaten  tes wird     l-Oxo-2-methyl-3-phenyl-propen-2     dargestellt durch Kondensation von     Benzal-          dehyd    mit     1-Oxo-propan    in organischen     Lö-          sungsmitteln    und in Gegenwart alkalischer  Stoffe und höchstens geringer Wasser  mengen.  



  In analoger Weise gelangt man zum     1-          Oxo-2-methyl-3-p-isopropyl-phenyl-propen-2,     wenn man im Verfahren des Hauptpatentes  den     Benzaldehyd    durch     4-Isopropylbenzal-          dehyd    ersetzt. Das bisher nicht bekannte     1-          O        xo-2-methyl-3-p-isopropyl    -     phenyl    -     propen-2     soll als Riechstoff oder zur Darstellung von  Riechstoffen Verwendung finden.  



       Beispiel:     Zu einer Lösung     vo%    1 Teil     Kalium-          hydroxyd    in 39 Teilen     Äthylalkohol    gibt  man 20 Teile     4-Isopropylbenzaldehyd    und  tropft im Laufe von drei bis     vier    Stunden  bei 10 bis<B>15'</B> 6 Teile     1-Oxo-propa.n    ein.

    Nach Entfernung des     gondensations-    und       Lösungsmittels    werden bei der     Destillation       im Vakuum ausser     i\Tebenproduktsn    erhalten       etwa    5 Teile     4-Isopropylbenzaldehyd    und  16 Teile     1-Oäy-2-methyl-3-p-isopropyl-pheriyl-          propen-2,    eine unter 9 mm Druck bei 152  bis 158   siedende gelbe Flüssigkeit von  würzigem Geruch.  



  Statt des Äthylalkohols     kann    man auch  andere Lösungsmittel verwenden, zum Bei  spiel     Methyl-    oder     Butylalkohol.  



  Process for the preparation of 1-oxo-2-ethyl-3-p-isopropyl-phenyl-propene-2. Cream: eat your method of the main godfather is l-oxo-2-methyl-3-phenyl-propene-2 represented by the condensation of benzaldehyde with 1-oxo-propane in organic solvents and in the presence of alkaline substances and at most less Amount of water.



  1-oxo-2-methyl-3-p-isopropyl-phenyl-propene-2 is obtained in an analogous manner if, in the process of the main patent, the benzaldehyde is replaced by 4-isopropylbenzaldehyde. The previously unknown 1-oxo-2-methyl-3-p-isopropyl-phenyl-propene-2 is intended to be used as a fragrance or for the representation of fragrances.



       Example: 20 parts of 4-isopropylbenzaldehyde are added to a solution of 1 part of potassium hydroxide in 39 parts of ethyl alcohol and 6 parts of 1-oxo are added dropwise over the course of three to four hours at 10 to <B> 15 '</B> propa.n a.

    After removal of the condensation and solvent, the distillation in vacuo gives about 5 parts of 4-isopropylbenzaldehyde and 16 parts of 1-oay-2-methyl-3-p-isopropyl-pheriyl-propene-2, one under 9 mm pressure at 152 to 158 boiling yellow liquid with a spicy odor.



  Instead of ethyl alcohol you can also use other solvents, for example methyl or butyl alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 1-Oxy- 2-methyl-3-p-isopropyl-phenyl-propen-2, da durch gekennzeichnet, dass man 4-Isopropyl- ben7,aldehyd mit 1-Oxo-propan in organi schen Lösungsmitteln und in Gegenwart alkalischer Stoffe und höchstens geringer Wassermengen kondensiert. Das Erzeugnis stellt eine gelbe Flüssigkeit dar, die unter 9 mm Druck bei 152 bis<B>158'</B> siedet. PATENT CLAIM: Process for the preparation of 1-oxy-2-methyl-3-p-isopropyl-phenyl-propene-2, characterized in that 4-isopropyl-ben7, aldehyde with 1-oxo-propane in organic solvents and condenses in the presence of alkaline substances and a maximum of small amounts of water. The product is a yellow liquid that boils at 152 to 158 'under 9 mm pressure.
CH133680D 1928-01-16 1928-01-16 Process for the preparation of 1-Ox0-2-methyl-3-p-isopropyl-phenyl-propene-2. CH133680A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH133680T 1928-01-16
CH125473T 1928-01-16

Publications (1)

Publication Number Publication Date
CH133680A true CH133680A (en) 1929-06-15

Family

ID=25710467

Family Applications (1)

Application Number Title Priority Date Filing Date
CH133680D CH133680A (en) 1928-01-16 1928-01-16 Process for the preparation of 1-Ox0-2-methyl-3-p-isopropyl-phenyl-propene-2.

Country Status (1)

Country Link
CH (1) CH133680A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0236700A1 (en) * 1986-01-23 1987-09-16 BASF Aktiengesellschaft Alpha,beta-substituted acroleins, process for their production and their use
EP0392258A2 (en) * 1989-04-12 1990-10-17 Firmenich Sa Aromatic aldehydes, their derivatives and their use as ingredients in perfumes, herbicides and fungicides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0236700A1 (en) * 1986-01-23 1987-09-16 BASF Aktiengesellschaft Alpha,beta-substituted acroleins, process for their production and their use
EP0392258A2 (en) * 1989-04-12 1990-10-17 Firmenich Sa Aromatic aldehydes, their derivatives and their use as ingredients in perfumes, herbicides and fungicides
EP0392258A3 (en) * 1989-04-12 1992-05-20 Firmenich Sa Aromatic aldehydes, their derivatives and their use as ingredients in perfumes, herbicides and fungicides

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