GB762067A - Novel esters and a process for the manufacture thereof - Google Patents

Novel esters and a process for the manufacture thereof

Info

Publication number
GB762067A
GB762067A GB8258/56A GB825856A GB762067A GB 762067 A GB762067 A GB 762067A GB 8258/56 A GB8258/56 A GB 8258/56A GB 825856 A GB825856 A GB 825856A GB 762067 A GB762067 A GB 762067A
Authority
GB
United Kingdom
Prior art keywords
ester
acid
trimethyl
methyl
oic
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
GB8258/56A
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB762067A publication Critical patent/GB762067A/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
    • C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises alkyl esters of 4-methyl - 6 - [21.61.61 - trimethyl-cyclohexen-(11)-yl] - hexadien - (2.4) - oic(1) acid in which the alkyl groups contain from 1 to 4 carbon atoms. They may be prepared by condensing 2-methyl-4 - [21.61.61 - trimethyl - cyclohexene - (11) - yl] buten - (2) - al(1) with a halogeno - acetic acid lower-alkyl ester and dehydrating the resulting 2.3 - epoxy - trimethyl - 6 - [21.61.61 - trimethylcyclohexen - (11) - yl] - hexen - (4) - oic(1) acid ester or 3 - hydroxy - 4 - methyl - 6 - [21.6.61-trimethylcyclohexen - (11) - yl] - hexen - (4) - oic(1) acid ester by heating in a solvent in the presence of an acidic dehydrating agent. The condensation step is carried out in known manner by using a metal, e.g. zinc or sodium, or an alkali-metal alcoholate, e.g. sodium methylate, as condensing agent. Preferably the condensation is carried out as a Reformatsky reaction using a bromo-acetic acid lower-alkyl ester. The product is a hydroxy ester. Alternatively the condensation may be carried out using a chloroacetic acid ester and sodium methylate in which case the product is an epoxy ester. The latter may be converted by heat into the corresponding keto-acid ester which may be reduced to the hydroxy ester. The dehydration of the hydroxy ester or the epoxy ester may be carried out by heating the ester in a solvent such as toluene or xylene in the presence of an acidic dehydrating agent such as p-toluene-sulphonic acid. In the example (a) a mixture of 2-methyl-4 - [21.61.61 - trimethyl - cyclohexene - (1)1 - yl]-buten - (2) - al - (1), bromo - acetic acid ethyl ester and ether are added to zinc to give 3-hydroxy - 4 - methyl - 6 - [21.61.61 - trimethyl-cyclohexen - (11) - yl] - hexen - (4) - oic - (1) - acid ethyl ester which is heated in toluene solution with p-toluene sulphonic acid to give 4-methyl-6 - [21.61.61 - trimethyl - cyclohexen - (11) - yl]-hexadien-(2.4)-oic-(1) acid ethyl ester. Specification 762,068 is referred to.
GB8258/56A 1953-07-07 1954-07-07 Novel esters and a process for the manufacture thereof Expired GB762067A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH762067X 1953-07-07

Publications (1)

Publication Number Publication Date
GB762067A true GB762067A (en) 1956-11-21

Family

ID=4534759

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8258/56A Expired GB762067A (en) 1953-07-07 1954-07-07 Novel esters and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB762067A (en)

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