Mild hydrolysis or alcoholysis of amides. Ti (IV) catalyzed conversion of primary carboxamides to carboxylic acids or esters

…, S Zaidi, CM Sorensen, ML Sparacino…

Index: Fisher; Caroon; Stabler; Lundberg; Zaidi; Sorensen; Sparacino; Muchowski Canadian Journal of Chemistry, 1994 , vol. 72, # 1 p. 142 - 145

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Citation Number: 26

Abstract

Reaction of primary amides (eg, 1 a or 6-13) or O-methylhydroxamates (1 b and 1 c) with a catalytic amount of TiCl4 and one equivalent of aqueous HCl converts these compounds in good yields to carboxylic esters (when an alcohol is used as solvent) or to carboxylic acids (when 9: 1 dioxane: H2O is used as solvent). These conversions are chemoselective for primary amides: mono-and dialkyl amides are not affected by the reaction conditions. The ...

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