Journal
SYNTHETIC COMMUNICATIONS
Volume 44, Issue 6, Pages 836-846Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2013.837485
Keywords
Amide; dehydration; esterification; hydrolysis; rehydration
Categories
Funding
- R. L. Fine Chemicals
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Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
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