GB719450A - A process for the preparation of unsaturated alicyclic 2-methyl butenal compounds - Google Patents

A process for the preparation of unsaturated alicyclic 2-methyl butenal compounds

Info

Publication number
GB719450A
GB719450A GB7659/54A GB765954A GB719450A GB 719450 A GB719450 A GB 719450A GB 7659/54 A GB7659/54 A GB 7659/54A GB 765954 A GB765954 A GB 765954A GB 719450 A GB719450 A GB 719450A
Authority
GB
United Kingdom
Prior art keywords
methyl
buten
hemi
acetal
dehydration
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
GB7659/54A
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.)
HOFFMANN LA ROCHE AG DEUTSCHE
Original Assignee
HOFFMANN LA ROCHE AG DEUTSCHE
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 HOFFMANN LA ROCHE AG DEUTSCHE filed Critical HOFFMANN LA ROCHE AG DEUTSCHE
Publication of GB719450A publication Critical patent/GB719450A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • 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
    • 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
    • C07C403/06—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 singly-bound oxygen atoms
    • C07C403/08—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 singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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
    • C07C2601/14—The ring being saturated
    • 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

Abstract

The invention comprises compounds of the formula: <FORM:0719450/IV (b)/1> where one R is methyl and the others are methyl or hydrogen. These are made from <FORM:0719450/IV (b)/2> where R1 is alkyl by partial hydrogenation, dehydration and acid cleavage of the product (an enol ether or hemi-acetal, formul being given). The starting materials are made as in Specification 719,417. In preferred operating conditions the hydrogenation is carried out using a palladium catalyst partially inactivated by lead and quinoline; the dehydration is effected with phosphorus oxychloride in toluene and pyridine, by passing the vapour over aluminium phosphate above 300 DEG C. or by heating with an organic acid such as toluene-p-sulphonic in an inert solvent. The last-named produces re-arrangement of the enol ether to a hemi-acetal and often effects cleavage to the aldehyde as well. Otherwise a separate step, e.g. standing with aqueous alcoholic sulphuric acid, is necessary. The products, which are intermediates in the synthesis of Vitamin A, may be purified by solvent extraction, distillation or chromatography. Examples show the production of 2-methyl-4-(21-methylcyclohexylidene) - buten - 2 - al and 2 - methyl-4 - (21 : 61 : 61 - trimethylcyclohexylidene)-buten-2-al. They are characterized as 2 : 4-dinitrophenylhydrazones.
GB7659/54A 1951-05-21 1952-05-16 A process for the preparation of unsaturated alicyclic 2-methyl butenal compounds Expired GB719450A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE719450X 1951-05-21

Publications (1)

Publication Number Publication Date
GB719450A true GB719450A (en) 1954-12-01

Family

ID=6627210

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7659/54A Expired GB719450A (en) 1951-05-21 1952-05-16 A process for the preparation of unsaturated alicyclic 2-methyl butenal compounds

Country Status (1)

Country Link
GB (1) GB719450A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3225102A (en) * 1960-12-13 1965-12-21 Eastman Kodak Co Allenic aldehydes
WO1989002885A1 (en) * 1987-09-23 1989-04-06 Basf K & F Corp. Alkyltetramethylcyclohexane derivatives and their use as perfumes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3225102A (en) * 1960-12-13 1965-12-21 Eastman Kodak Co Allenic aldehydes
WO1989002885A1 (en) * 1987-09-23 1989-04-06 Basf K & F Corp. Alkyltetramethylcyclohexane derivatives and their use as perfumes
US4868339A (en) * 1987-09-23 1989-09-19 Basf K & F Corporation Alkyltetramethylcyclohexane derivatives and their use as perfumes

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