GB784891A - Novel unsaturated ketones and a process for the manufacture thereof - Google Patents

Novel unsaturated ketones and a process for the manufacture thereof

Info

Publication number
GB784891A
GB784891A GB26185/55A GB2618555A GB784891A GB 784891 A GB784891 A GB 784891A GB 26185/55 A GB26185/55 A GB 26185/55A GB 2618555 A GB2618555 A GB 2618555A GB 784891 A GB784891 A GB 784891A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
cyclohexen
alkyl
methyl
acid
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
Application number
GB26185/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB784891A publication Critical patent/GB784891A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
    • C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • C07C45/676—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 change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises ketones of the general formula <FORM:0784891/IV (a)/1> wherein R stands for a 6-alkyl-2,6-dimethyl-cyclohexen-(1)-yl- or 6-alkyl-2,6-dimethyl-cyclo hexen-(2)-yl radical wherein the alkyl radical contains from 2 to 4 carbon atoms. The compounds of the above formula in which R stands for a 6 - alkyl - 2,6 - dimethyl - cyclohexen - (1)-yl radical are prepared by treating a ketone of the general formula <FORM:0784891/IV (a)/2> wherein R1 represents an alkyl radical having from 2 to 4 carbon atoms, with substantially water free sulphuric acid at below 0 DEG C. The compoudds of the above formula in which R stands for a 6-alkyl-2,6-dimethyl-cyclohexen-(2)-yl radical wherein the alkyl group contains from 2 to 4 carbon atoms are prepared by treating the starting material ketone of the above general formula with phosphonic acid at about 20-35 DEG C. In examples: 4-[61-ethyl-21,61dimethyl - cyclohexen - (11) - yl] - buten - (3)-one-(2) is obtained by adding 6,10-dimethyl-dodecatrien - (3,5,9) - one - (2) to a mixture of concentrated sulphuric acid and glacial acetic acid (1); 4-[61-ethyl-21,61-dimethyl -cyclohexen-(21) - yl] - buten - (3) - one - (2) is obtained by employing 85 per cent phosphoric acid in a similar process (2); 4 - [61 - isobutyl - 21,61 - dimethyl - cyclohexen - (2) - yl] - buten - (3)-one-(2) is obtained from 6,10,12-trimethyl-tridecatrien-(3,5,9)-one-(2) in a similar process (3); 4 - [61 - isobutyl - 21,61 - dimethyl - cyclohexen - (11) - yl] - buten - (3) - one - (2) is obtained by adding 6,10,12-trimethyldecatrien-(3,5,9)-one-(2) to a cooled mixture of sulphuric acid and glacial acetic acid. 6,10-Dimethyl-dodecatrien-(3,5,9)-one-(2) is obtained by converting 1-chloro-3-methyl pentene-(2) with hydrochloric acid to 1 - chloro - 3 - methyl - pentene - (2) which is reacted with ethyl acetoacetate and sodium methylate to form 3-carbethoxy-6-methyl-octen-(5)-one-(2) which is converted with alcoholic potassium hydroxide to the potassium salt of 3 - carboxy - 6 - methyl - octen - (5)-one-(2) which is acidified and fractionated to obtain 6 - methyl - octen - (5) - one - (2) which with lithium acetylide and acetylene yields 3,7-dimethyl-nonen-(6)-yn-(1)-ol-(3) which is hydrogenated in the presence of a lead/palladium/calcium carbonate catalyst to obtain 3,7-dimethyl-non-dien-(1,6)-ol-(3) which is treated with sodium dichromate and sulphuric acid to obtain 3,7-dimethyl-nonadien-(2,6)-ol-(1) which is treated with acetone and aluminium isopropylate and acid to obtain the desired ketone. Other starting material ketones may be similarly obtained, e.g. by using 3,5-dimethyl-hexen-(1)-ol-(3) instead of 3-methyl-penten-(1)-ol-(3).
GB26185/55A 1954-09-13 1955-09-13 Novel unsaturated ketones and a process for the manufacture thereof Expired GB784891A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US784891XA 1954-09-13 1954-09-13

Publications (1)

Publication Number Publication Date
GB784891A true GB784891A (en) 1957-10-16

Family

ID=22144341

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26185/55A Expired GB784891A (en) 1954-09-13 1955-09-13 Novel unsaturated ketones and a process for the manufacture thereof

Country Status (2)

Country Link
FR (1) FR1130887A (en)
GB (1) GB784891A (en)

Also Published As

Publication number Publication date
FR1130887A (en) 1957-02-13

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