A simple procedure for the esterification of alcohols with sodium carboxylate salts using 1-tosylimidazole (TsIm)

An efficient and selective method for esterification of alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of RCO2Na (R: alkyl and aryl), TsIm, and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DNIF to afford the corresponding esters in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1 degrees > 2 degrees > 3 degrees. (C) 2007 Elsevier Ltd. All rights reserved.