A Convenient Procedure for the Hydrolysis of Hindered Esters

Abstract

Although several procedures for the hydrolysis of hindered esters have been developed, most of them suffer from one or more disadvantages, either in lack of convenience or in stringent conditions which affect other functional groups. Among the presently available methods for effecting this conversion are lithium in ammonia, a strong reducing agent¹; boron trichloride, a Lewis acid²; and a variety of reagents which bring about alkyl-oxygen cleavage. Among the latter are lithium iodide in a variety of solvents, usually at elevated temperatures, or in the presence of an organic base³; 1,5-diazabicyclo [4, 3, 0] nonene-5, in boiling xylene⁴, a reaction which failed in this laboratory⁵; various mercaptides^6,7, which in addition to being experimentally offensive, also cleave aryl alkyl ethers.