A novel aromatisation reaction of derivatives of 1,2-O-isopropylidene-myo-inositol

Abstract

Tetra-O-alkyl ethers of 1,2-O-isopropylidene-myo-inositol are converted into 1,2,4-trialkoxybenzenes on treatment with potassium t-butoxide in dimethyl sulphoxide at 80°. An intermediate product in the conversion of 3,4,5,6-tetra-O-benzyl-1,2-O-isopropylidene-myo-inositol into 1,2,4-trisbenzyloxybenzene was isolated. The intermediate, 3,4,5,6-tetrakisbenzyloxycyclohex-2-enol, was converted into 4,5,6-trisbenzyloxycyclohex-2-enone on treatment with acid and the latter compound gave 2,4-bisbenzyloxyphenol after treatment with base.