Chemistry of quinones. Part III. Cleavage of the methyl ethers of some naturally occurring hydroxyanthraquinones

Abstract

The action of the reagent formed by adding water (3 equiv.) to potassium t-butoxide (10 equiv.) in 1,2-dimethoxyethane on the methyl ethers of a range of naturally occurring mono-, di-, and tri-hydroxy-β-methylanthraquinones has been studied. All the substrates containing at least one α-methoxy-substituent were cleaved to give mixtures of benzoic acids and/or phthalic acids in 42–82% yield.