Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran–Water in the Presence of Sodium Hydroxide

Abstract Oligoethylene glycols and some related alcohols were efficiently tosylated with p-toluenesulfonyl chloride in a tetrahydrofuran–water (1:1) mixture in the presence of excess sodium hydroxide. This method is advantageous over the conventional tosylation in pyridine both regarding the work-up procedure, the yield, and the purity of the product, and may be potentially useful for the tosylation of certain acid-labile alcohols.