Tetrahedron

Benzylation of hydroxy groups with tertiary amine as a base

JW Gathirwa, T Maki

Index: Gathirwa, Jeremiah W.; Maki, Toshihide Tetrahedron, 2012 , vol. 68, # 1 p. 370 - 375

Full Text: HTML

Citation Number: 18

Abstract

The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150° C. Sodium iodide was found to ...