Metal-ammonia reduction of some acyl phenols

Abstract

2- and 4-Hydroxyacetophenone on reduction with metal-ammonia solutions give mainly pinacols with some of the alcohol; 3-hydroxyacetophenone gives no pinacol. In no case is hydrogenolysis of the side-chain oxygen observed. 4-Hydroxy-propiophenone gives a good yield of a mixture of stereoisomeric pinacols related to hexoestrol.