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.

• Authors: Yoshio Kasashima, Atsushi Uzawa, Kahoko Hashimoto, Yu Yokoyama, Takashi Mino, Masami Sakamoto, Tsutomu Fujita
• Journal: Journal of oleo science (J Oleo Sci) Vol. 59 Issue 11 Pg. 607-13 ( 2010) ISSN: 1347-3352 [Electronic] Japan
• PMID: 20972361 (Publication Type: Journal Article)

Chemical References

• Amides
• Benzyl Alcohols
• Camphanes
• Nitriles
• Solvents
• Iodine
• benzonitrile
• methylphenyl carbinol
• isoborneol

Topics

• Amides (chemical synthesis)
• Benzyl Alcohols (chemistry)
• Camphanes (chemistry)
• Catalysis
• Dehydration
• Iodine
• Nitriles (chemistry)
• Organic Chemistry Phenomena
• Solvents
• Stereoisomerism
• Temperature