GB567438A - Manufacture of cyclic ketones - Google Patents

Manufacture of cyclic ketones

Info

Publication number
GB567438A
GB567438A GB1098343A GB1098343A GB567438A GB 567438 A GB567438 A GB 567438A GB 1098343 A GB1098343 A GB 1098343A GB 1098343 A GB1098343 A GB 1098343A GB 567438 A GB567438 A GB 567438A
Authority
GB
United Kingdom
Prior art keywords
acid
ester
methyl
thiolpropionic
substituted
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
GB1098343A
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.)
ANTHONY WILLIAM D AUBIGNY AVIS
Roche Products Ltd
Original Assignee
ANTHONY WILLIAM D AUBIGNY AVIS
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 ANTHONY WILLIAM D AUBIGNY AVIS, Roche Products Ltd filed Critical ANTHONY WILLIAM D AUBIGNY AVIS
Priority to GB1098343A priority Critical patent/GB567438A/en
Publication of GB567438A publication Critical patent/GB567438A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

2-Substituted - 3 - ketotetrahydrothiophenes and their 4-carboxylic acid ester derivatives. Compounds of the formula <FORM:0567438/IV/1> in which R represents an alkyl group and X an alkyl, aryl, substituted alkyl or fatty acid ester residue are obtained by reaction of S-(carbalkoxy-methyl)-thiolpropionic acid esters of the formula ROOC.CH2.CH2.S.CHX.COOR1 wherein R and R1 represent alkyl groups and X has the meaning given above, with alkali metals or their amides or alcoholates. The tetrahydrothiophene derivatives, on hydrolysis and decarboxylation, by methods known for the ketonic cleavage of b -ketone esters, yield 2-substituted-3-ketotetrahydrothiophenes of the formula <FORM:0567438/IV/2> wherein X has the meaning given above and may also represent a fatty acid residue. In examples: 2 - methyl - 3 - ketotetrahydrothio - phene and its 4-carbethoxy derivative are prepared from S - (methyl - carbethoxymethyl) - thiolpropionic acid ethyl ester, g -(3-ketotetrahydrothiophene-2) - butyric acid, its ethyl ester and the 4-carbethoxy derivative thereof, from diethyl S - (2 - carbethoxyethyl) - a - thioladipate, and #s- (3 - ketotetrahydrothiophene - 2) - valeric acid and the 4-carbethoxy derivative of its ethyl ester from diethyl S-(2-carbethoxyethyl)-a -thiolpimelate. In each case the condensation is effected by heating with sodium in benzene under reflux. Identification of the acids by the p-phenylphenacyl ester and the benzylthiuronium salt is referred to. The S-(carbalkoxy-methyl)-thiolpropionic acid esters are prepared by reaction of an alkali metal salt of b -thiolpropionic acid with an appropriate a -halogen acid ester or alkali metal salt and esterification of the resulting acid or half-ester. Specification 562,313 is referred to.
GB1098343A 1943-07-06 1943-07-06 Manufacture of cyclic ketones Expired GB567438A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1098343A GB567438A (en) 1943-07-06 1943-07-06 Manufacture of cyclic ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1098343A GB567438A (en) 1943-07-06 1943-07-06 Manufacture of cyclic ketones

Publications (1)

Publication Number Publication Date
GB567438A true GB567438A (en) 1945-02-14

Family

ID=9977883

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1098343A Expired GB567438A (en) 1943-07-06 1943-07-06 Manufacture of cyclic ketones

Country Status (1)

Country Link
GB (1) GB567438A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2475580A (en) * 1945-06-21 1949-07-12 American Cyanamid Co Keto thiophanes and method of preparing same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2475580A (en) * 1945-06-21 1949-07-12 American Cyanamid Co Keto thiophanes and method of preparing same

Similar Documents

Publication Publication Date Title
GB567438A (en) Manufacture of cyclic ketones
GB1496491A (en) Dihydroergopeptine derivatives
US2537892A (en) Esters of 2-benzamido-3-carboxymethylmercapto-propanoic acid
US2228256A (en) Substituted malonic acid derivatives and process of preparing them
US2466232A (en) Synthesis of biotin intermediates
ES337591A1 (en) Novel acrylic acid derivatives and process for the preparation thereof
US2451427A (en) Hydroxythiophane carboxylic acids and esters and methods of preparing same
GB1382267A (en) Phenylalkanoic acid derivatives
US2470739A (en) Carboxythiophanes and method of preparing same
GB593024A (en) Production of ª‰-2-thienoylpropionic acids and derivatives thereof
US2475580A (en) Keto thiophanes and method of preparing same
GB1429287A (en) Process for the preparation of 3-alkyl-cyclopentane-1,2-diones and intermediates therefor
ES363419A1 (en) Preparation of phenylalanine derivatives and novel intermediates
GB1180208A (en) 5-Nitrofuran Derivatives
US2673849A (en) Substituted thiobarbituric acids
SU97002A1 (en) Method for preparing omega cyanoacetophenone derivatives
GB644406A (en) Improvements in or relating to the dehydration of hydroxylated fatty acid esters
GB1263768A (en) New substituted aryloxy- and arylthioacetic acids, esters and salts thereof, process for their production and compositions containing same
GB570240A (en) A process for the manufacture of thiophane-3-one-carboxylic acid esters and of thiophane-3-one
GB811700A (en) Process for the production of heterocyclic carboxylic acids of the pyrazolidine series as well as the esters and salts thereof
GB553305A (en) Improvements in and relating to the production of unsaturated ketones and their related keto alcohols
GB777754A (en) A method of preparing a new hydroxycoumarin derivative with anticoagulating properties
GB1034788A (en) Process for the production of salts of substituted ª‡-amino carboxylic acids
GB772215A (en) Process for the production of new di-acylated tartaric acids
ES450472A1 (en) Benzoyl pyrazole 5-acetic acid derivatives useful as uricosurucs