Thionyl chloride (SOCl2) has been extensively used as a chlorinating reagent for the esterification of carboxylic acids via the formation of an acid chloride intermediate. While SOCl2-mediated deacetylation of acetoxy (O-deacetylation) and acetamido (N-deacetylation) esters is rare and has been reported on a coumarin substrate, deacetylation of thioacetate (S-deacetylation) esters by SOCl2 is unknown. Furthermore, a simultaneous deacetylation and esterification of acetoxy, acetamido, and thioacetate carboxylic acids in a one-pot synthetic scheme has not been reported in the literature. We report deacetylation and esterification of a diverse series of acetoxy carboxylic acids mediated by SOCl2, with examples from acetamido and thioacetate carboxylic acids to obtain hydroxy, amino, and thiol esters in a one-pot procedure. The reaction can be conveniently carried out at room temperature for 8-18 h, followed by an aqueous workup in good to excellent yields and has a very broad substrate scope.
Khaliq et al. (Tue,) studied this question.