American Chemical Society
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Regioselective Hydrolysis and Transesterification of Dimethyl 3‑Benzamidophthalates Assisted by a Neighboring Amide Group

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posted on 2016-06-09, 00:00 authored by Marko Krivec, Franc Perdih, Janez Košmrlj, Marijan Kočevar
An efficient, highly regioselective hydrolysis and transesterification of dimethyl 3-benzamidophthalates into the corresponding carboxylic acid monoesters and mixed esters (including tert-butyl esters) under basic conditions is presented. The selectivity is governed by the neighboring 3-benzamido moiety’s participation and by the nature of the solvent. In alcohols the reaction occurred exclusively at the ortho-position to the benzamido functionality, in pyridine or acetonitrile at both ester groups. An insight into the mechanistic pathway was obtained from a 1H NMR study in perdeuteromethanol.