STUDIES IN THE POLYOXYPHENOL SERIES: V. PREPARATION FROM PYROGALLOL OF THE ISOMERIC CYCLOHEXANE-1,2,3-TRIOLS AND -1,2-DIOLS, AND OF SEVERAL ISOPROPYLIDENE AND MONOMETHYL DERIVATIVES

Abstract

A study of the high pressure hydrogenation of pyrogallol over nickel, copper – chromium oxide, and palladium catalysts showed that yields of 35% to about 60% of cis-cis-cis-cyclohexane-l,2,3-triol were attainable, but that the cis-cis-trans and cis-trans-cis isomers were formed only in minor amount. Partial hydrogenolysis of these primary products incidentally yielded some cis-cyclohexane-l,2-diol, a smaller amount of the trans form, but none of the 1,3-diols. The following derivatives were prepared apparently for the first time: cis-cis-isopropylidene-cis-cyclohexane-l,2,3-triol, an oil, and its monobenzoate, m.p. 103 °C.; cis-cis-isopropylidene-trans-cyclohexane-l,2,3-triol, m.p. 51°C., and its monobenzoate, m.p. 72° to 76°C.; cis-monomethyl-cis-cis-cyclohexanetriol, m.p. 71°C., and its bis-3,5-dinitrobenzoate, m.p. 190°C.; trans-monomethyl-cis-cis-cyclohexane-l,2,3-triol, m.p. 37°C.;and isopropylidene-trans-cyclohexane-1,2-diol, an oil. Formation of the latter compound occurred when p-toluene-sulphonic acid, and not the customary hydrogen chloride, was used as catalyst in the condensation of the trans diol with acetone.