Reductive removal by sodium borohydride of side-chain oxygen from phenolic ketones

Abstract

The reduction of a variety of phenolic carbonyl compounds with boiling aqueous alkaline sodium borohydride has been studied. When the carbonyl group is ortho or para to a phenolic hydroxyl, reduction proceeds to the methylene derivative, but stops at the carbinol stage when the phenolic hydroxyl and carbonyl group are meta oriented.     The simplicity and selectivity of the reaction makes it of synthetic value.