GB639888A - The manufacture of aldehydes from ketones related to ª‰-ionone - Google Patents

The manufacture of aldehydes from ketones related to ª‰-ionone

Info

Publication number
GB639888A
GB639888A GB33381/47A GB3338147A GB639888A GB 639888 A GB639888 A GB 639888A GB 33381/47 A GB33381/47 A GB 33381/47A GB 3338147 A GB3338147 A GB 3338147A GB 639888 A GB639888 A GB 639888A
Authority
GB
United Kingdom
Prior art keywords
ionone
semicarbazone
ketones
formula
methyl
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
GB33381/47A
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
Hoffmann La Roche Inc
Original Assignee
F Hoffmann La Roche AG
Hoffmann La Roche Inc
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, Hoffmann La Roche Inc filed Critical F Hoffmann La Roche AG
Priority to GB33381/47A priority Critical patent/GB639888A/en
Publication of GB639888A publication Critical patent/GB639888A/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
    • 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)
  • Fats And Perfumes (AREA)

Abstract

The process of the parent Specification is applied to 2-(methylcyclohexenyl)-vinyl alkyl ketones (other than b -ionone) and 2-(methylcyclohexadienyl)-vinyl alkyl ketones and compounds derived from these by opening the ring at the 11-position, these ketones being condensed with a halogeno-acetic ester and the product treated with an alkali to produce a 4-substituted-2-alkyl-butene-(2)-al-(1), the whole process being carried out without the application of external heat; the alkyl group in the ketone starting material has 4 or less carbon atoms. Suitable starting materials are pseudo-ionone, a -ionone, dehydro - b - ionone, b - methylionone of the formula <FORM:0639888/IV (b)/1> and cyclic homologues of b -ionone of the formula <FORM:0639888/IV (b)/2> where R is hydrogen or methyl, one at least being hydrogen. Chloracetic esters are preferably used, and the temperature is not allowed to rise above 50 DEG C. at any time. The aldehydes obtained are extracted from the reaction mixture with a substantially water-immiscible liquid and may be characterised as the phenyl-semicarbazone or the thio-semicarbazone. Examples show the treatment of pseudo-ionone and of a -ionone, the phenyl-semicarbazone of the product from the former being described. Dehydro-b -ionone is obtained from 2 : 6 : 6-trimethylcyclohexadiene - (1 : 3) - al - (1) and acetone, or by the dehydrogenation of b -ionone. b -Methyl-ionone of the formula given above is produced by the ring-closure of pseudomethylionone with sulphuric acid, the latter ketone being obtained by condensing citral with methyl ethyl ketone. The cyclic homologues of b -ionone are prepared by reacting acetylene with cyclohexanone or a methylcyclohexanone, dehydrating, forming the Grignard reagent, treating this with acetic anhydride and partially dehydrogenating.
GB33381/47A 1947-12-18 1947-12-18 The manufacture of aldehydes from ketones related to ª‰-ionone Expired GB639888A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB33381/47A GB639888A (en) 1947-12-18 1947-12-18 The manufacture of aldehydes from ketones related to ª‰-ionone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB33381/47A GB639888A (en) 1947-12-18 1947-12-18 The manufacture of aldehydes from ketones related to ª‰-ionone

Publications (1)

Publication Number Publication Date
GB639888A true GB639888A (en) 1950-07-05

Family

ID=10352199

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33381/47A Expired GB639888A (en) 1947-12-18 1947-12-18 The manufacture of aldehydes from ketones related to ª‰-ionone

Country Status (1)

Country Link
GB (1) GB639888A (en)

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