Amidation of alcohols with nitriles under solvent-free conditions using molecular iodine as a catalyst

Abstract

The reactions of alcohols with nitriles under solvent-free conditions, using molecular iodine as a catalyst, were investigated. The reaction of 1-phenylethanol with propanenitrile produced the amide N-(1-phenylethyl)propanamide, by dehydration and tautomerization, in 71% yield, under the following conditions: temperature = 90°C, alcohol:iodine molar ratio = 1:0.2, alcohol:nitrile molar ratio = 1:5, and reaction time = 5 h. The amidation reactivity depended on the stability of the cationic intermediate formed from the alcohol. The reaction of (-)-borneol with benzonitrile produced a racemic amide in 83% yield. © 2010 by Japan Oil Chemists' Society.