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)

Similar Documents

Publication Publication Date Title
GB1057117A (en) Processes for preparing steroids compounds and the compounds when thus prepared
GB762067A (en) Novel esters and a process for the manufacture thereof
GB762041A (en) Novel hydroxy-esters and the manufacture and conversion thereof
GB1071818A (en) Novel indane derivatives and processes for their preparation
GB1038346A (en) Processes for preparing 2-alkyl-cyclopentane derivatives, and the derivatives thus prepared
GB762068A (en) A novel alcohol and a process for the manufacture thereof
GB1530422A (en) 4-(2,6,6-trimethyl-1-cyclohexen-1-ylidene)-butan-2-ol
ES429957A1 (en) Process for the preparation of an ester of an alkyl-or alkenyl succinic acid and a polyvalent alcohol
GB828202A (en) Improvements in or relating to manufacture of rosin size
GB871277A (en) Novel unsaturated ethers and a process for the manufacture and conversion thereof
ES439296A1 (en) Process for the preparation of maleic anhydride from maleic acid in the presence of sulfolane
GB1235535A (en) Novel a-nor-estra-5(10),9(11)-dien-2-ones, and processes for their preparation
GB728943A (en) Novel coumarin derivatives and a process for the manufacture thereof
GB1039744A (en) Process for the preparation of adiponitrile
GB569100A (en) Improvements in or relating to guanamines and methods of preparing the same
ES334803A1 (en) A procedure for the preparation of 3-oxo 13 beta-r 17 beta-ox 2-oxa 4,9,11-gonatrienes. (Machine-translation by Google Translate, not legally binding)
GB914732A (en) New cyclopentano-naphthalene derivatives and their formation
GB914734A (en) New cyclopentano-naphthalene derivatives and their formation
GB745045A (en) Improvements in methods of manufacturing -a-ionylidene ethanol and -a-ionylidene acetaldehyde
GB885766A (en) Cyclic esters of arylboronic acids and processes for their preparation
GB807101A (en) Isomers of pseudoirones substituted at c, and/or c
GB882592A (en) Process for the synthesis of 4-hydroxy-tryptophan
GB802570A (en) Novel carotenoids and a process for the manufacture thereof
GB613705A (en) Process of preparing new substituted thiobarbituric acids
GB601789A (en) Process for producing ascorbic acid from derivatives of l-keto-2 gulonic acid