Green Chemistry

A flexible Pinner preparation of orthoesters: the model case of trimethylorthobenzoate

M Noè, A Perosa, M Selva

Index: Noe, Marco; Perosa, Alvise; Selva, Maurizio Green Chemistry, 2013 , vol. 15, # 8 p. 2252 - 2260

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Citation Number: 6

Abstract

In the absence of additional solvents, a novel procedure was implemented for the synthesis of trimethylorthoesters through the Pinner reaction. At 5° C, the reaction of both aliphatic and aromatic nitriles (RCN; R= Et, Bu, Ph) with a moderate excess of MeOH and gaseous HCl gave the corresponding imidate hydrochlorides [RC (NH) OR′· HCl] in excellent yields (> 90%). At 25–65° C, the methanolysis of alkyl imidate salts provided trimethylortho- ...