Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

作者:Kasashima Yoshio*; Uzawa Atsushi; Hashimoto Kahoko; Yokoyama Yu; Mino Takashi; Sakamoto Masami; Fujita Tsutomu
来源:Journal of Oleo Science, 2010, 59(11): 607-613.
DOI:10.5650/jos.59.607

摘要

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 degrees 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.

  • 出版日期2010-11