Benzyl Chloride → Methyl beta-D-glucopyranoside

Participants

Reaction Conditions

Reaction Steps

A general procedure according to S. Koto et al. (Bull. Chem. Soc. Japan, (1976), 49:2939-40) was followed. A suspension of methyl-α-D-glucopyranoside (Aldrich, 5.02 g, 0.0259 mol), sodium hydride (Aldrich, 4.31 g, 0.1796 mol) and benzyl chloride (Aldrich, 125 ml, 25:1 (v/w) vs carbohydrate) was stirred vigorously and heated to a bath temperature of 115° C. whereupon the gray reaction mixture thickened and an exotherm occurred. The reaction mixture reached 135° C. and turned into a thin, yellowish slurry. The reaction was allowed to stir at this temperature for 1 h. The insoluble material was removed by filtration and the solution concentrated in vacuo. Flash chromatography on silica gel (E. M. Science, 230-400 mesh) using methylene chloride as eluant gave the product (Rf value: 0.63) as an oil (7.45 g, 52%). 1H NMR data (CDCl3): δ7.27 (m, 20H, aromatic H on benzyl group), 3.45 (s, 3H, --OCH3 ).

Provenance & Evidence