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Studies on cyclohexane derivatives: II. Preparation and chemical proof of the configuration of the two 4-methylcyclohexanecarboxylic acids

✍ Scribed by H. van Bekkum; A. A. B. Kleis; A. A. Massier; D. Medema; P. E. Verkade; B. M. Wepster

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
777 KB
Volume
80
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The preparation of pure low‐melting 4‐methylcyclohexanecarboxylic acid (m.p. 30.5‐31.5°) is described for the first time.

By chemical means it is proved that low‐melting 4‐methylcyclohexanecarboxylic acid possesses the cis‐configuration and the high‐melting isomer the trans‐configuration. For this purpose these acids were converted into cis‐ and trans‐1,4‐dimethylcyclohexane respectively, using reactions which take place without any change of configuration at the cyclohexane nucleus. The configuration of these two hydrocarbons has been proved in the first paper of this series.

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