Reactions with thioethoxide ion in dimethylformamide. II. O-Alkyl cleavage of methylene ethers, methyl esters, and aryloxyacetates

Abstract

Reaction of 1,3-benzodioxole with sodium thioethoxide in DMF gave a good yield of ethyl o-hydroxyphenoxymethyl sulphide (3), which was converted into catechol nearly quantitatively by acid treatment. The same reagent converted methyl p-anisate into p-hydroxybenzoic acid, and methyl p-chlorophenoxyacetate to p-chlorophenol in good yield, indicating its usefulness in cleaving methyl esters and aryloxyacetates respectively.