GB634924A - Process for the synthesis of ketones of the vitamin a series - Google Patents

Process for the synthesis of ketones of the vitamin a series

Info

Publication number
GB634924A
GB634924A GB26911/46A GB2691146A GB634924A GB 634924 A GB634924 A GB 634924A GB 26911/46 A GB26911/46 A GB 26911/46A GB 2691146 A GB2691146 A GB 2691146A GB 634924 A GB634924 A GB 634924A
Authority
GB
United Kingdom
Prior art keywords
ionylidene
ketone
group
methyl
condensation
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
GB26911/46A
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.)
Organon NV
Original Assignee
Organon NV
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 Organon NV filed Critical Organon NV
Publication of GB634924A publication Critical patent/GB634924A/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
    • 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)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Ketones of the vitamin A series are obtained by reacting compounds of the general formula R=X-Ac, in which R is the b -ionylidene group or a group which may be easily converted to the b -ionylidene group, X stands for the group =CH-CH=CH- and Ac is a carboxyl group or a functional derivative thereof, with a reactive organo-metallic compound capable of introducing an alkyl group. An example is given of the preparation of a ketone (C18) by condensing b -ionylidene crotonic acid with methyl lithium. In addition there may be used alkyl magnesium halogenides as the organo-metallic compound. Specification 634,925 is referred to. Samples have been furnished under Sect. 2 (5) of the C18 ketone prepared by using ionylidene crotonyl chloride and dimethyl cadmium and of the C20 ketone prepared from b -ionylidene crotonic acid using propyl chloride and lithium. b -Ionylidene crotonic acid is obtained by the condensation of b -ionone with methyl g -bromocrotonate under the influence of zinc, followed by the saponification of the dehydrated ester. Dimethyl cadmium is obtained by treating methyl magnesium bromide with cadmium bromide. The Specification as open to inspection under Sect. 91 comprises the manufacture of ketones from starting materials in which X is an unsaturated hydrocarbon group containing a carbon chain in which double bonds are arranged in such a way that a continuous series of double bonds exists between those in R and the one in the C=O group, and also includes additional examples describing (1) the production of the C16 ketone by condensation of b -ionylidene acetonitrile with methyl magnesium bromide; (2) the preparation of the C18 ketone by condensation of p-ionylidene crotonitrile with methyl magnesium bromide; (3) the preparation of the C18-ketone by condensation of b -ionylidene crotonamide with methyl magnesium bromide; (4) the preparation of the C21 ketone from vitamin A acid using methyl lithium. This subject-matter does not appear in the Specification as accepted.
GB26911/46A 1945-09-07 1946-09-06 Process for the synthesis of ketones of the vitamin a series Expired GB634924A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL634924X 1945-09-07

Publications (1)

Publication Number Publication Date
GB634924A true GB634924A (en) 1950-03-29

Family

ID=19788856

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26911/46A Expired GB634924A (en) 1945-09-07 1946-09-06 Process for the synthesis of ketones of the vitamin a series

Country Status (1)

Country Link
GB (1) GB634924A (en)

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