A mechanistic study of the base-catalyzed methanolysis and hydrolysis of the hydrogen phthalate ester of 4-bromo-4′-nitrobenzhydrol

The hydrogen phthalate ester of 4-bromo-4′-nitrobenzhydrol has been subjected to base-catalyzed methanolysis and hydrolysis. In both cases the BAC2 mechanism has been observed. There is no evidence of ortho-carboxylate anion participation (BAC1 mechanism). The results have been substantiated by kinetics, stereochemistry, and 18O isotope studies.