Reductive Alkylation of Benzoates Containing Benzylic Oxygen

Abstract

Several methyl benzoates derivatives containing oxygen at the benzylic position were subjected to reductive alkylations using lithium at -65°C in liquid ammonia (a Birch reduction). It was found that the methyl benzoate derivatives that had the benzylic oxygen meta to the methyl ester survived the reduction whereas those that had the benzylic oxygen othro or para to the ester underwent benzylic cleavage and/or reduction of the ester functional group.