Preparation of trans-4-alkyl-cyanoarylcyclohexanes

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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252299, 260544P, 260558R, 560102, 562492, C07C12164

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active

042293677

ABSTRACT:
Trans-4-alkyl-cyanoarylcyclohexanes are prepared in a stereoselective manner from arylcarboxylic acids of the formula Ar-[Ar].sub.n -Ar-4-COOH, Ar being aryl and n being 0 to 2, by first converting such a carboxylic acid to a mixture of the cis and trans isomers of the corresponding cyclohexa-2,5-diene-4-carboxylic acid, esterifying the resulting isomer mixture with a lower alkanol and further hydrogenating the resulting esters/isomers to produce the cis and trans isomers of the corresponding cyclohexane-4-carboxylic acid esters, isomerizing the cis isomers in the mixture to the trans isomer thereby producing a mixture containing the trans isomer substantially free from cis isomer, stereospecifically saponifying the trans isomer, growing a carbon chain of desired length on the carboxyl group of the resulting carboxylic acid, reducing the carbonyl group thereof, and introducing a cyano group into the terminal aryl group. The resulting product is useful as a nematic liquid crystal.

REFERENCES:
patent: 3852286 (1974-12-01), Hall et al.
patent: 4016204 (1977-04-01), Rajadhyaksha
patent: 4130502 (1978-12-01), Eidenschink et al.

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