Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Isomers of the Hydrogenation Products of Bisphenol A. The Separations and Configurations of Three Isomers of 2,2-Bis-(4-hydroxycyclohexyl)propane and Two of 2-(4-Hydroxycyclohexyl)-2-(p-hydroxyphenyl)propane
Akira Terada
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1966 Volume 39 Issue 10 Pages 2194-2201

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Abstract

Hydrogenations of bisphenol A (I) over Raney nickel (W-1) and Urushibara nickel A and B have been carried out, and three stereoisomers of 2,2-bis(4-hydroxycyclohexyl)propane (II) and two of 2-(4-hydroxycyclohexyl)-2-(p-hydroxyphenyl)propane (III) have been isolated from the products. The configurations and the preferred conformations of the II isomers, cis-cis (m. p. 174–175°C), cis-trans (164–165.5°C) and trans-trans (188–189°C), and of the III isomers, cis (159–161°C) and trans (150.5–151.5°C), have been determined by means of the infrared and nuclear magnetic resonance spectra, inversions over sodium to the stable isomers, and other methods. When heated with purified methanol, 2,2-bis(4-ketocyclohexyl)propane prepared from the chromium trioxide oxidation of an isomeric mixture of II afforded 2,2-bis(4,4-dimethoxycyclo-hexyl)propane, m. p. 140.5–141.5°C. The recrystallization of IIIt from benzene yielded IIIt·C6H6. Treating IIIc with acetic anhydride gave 2-(3-cyclohexenyl)-2-(p-hydroxyphenyl)propane (where c: cis and t: trans).

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