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Simple One-Pot Conversion of Alcohols into Nitriles

Hiroyuki Shimojo, Katsuhiko Moriyama, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email:

H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2013, 45, 2155-2156.

DOI: 10.1055/s-0033-1338489


Various alcohols were efficiently converted into the corresponding nitriles at room temperature by treatment with tert-butyl hypochlorite, diiodine, or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in the presence of TEMPO, followed by treatment with diiodine and aqueous ammonia. The nitriles were obtained in good yields and high purities by a simple extraction of the reaction mixture with chloroform and subsequent removal of the solvent.

see article for more examples

Oxidative Conversion of Primary Alcohols, and Primary, Secondary, and Tertiary Amines into the Corresponding Nitriles with 1,3-Diiodo-5,5-dimethylhydantoin in Aqueous NH3

S. Iida, H. Togo, Synlett, 2007, 407-410.

Key Words

nitriles, alcohols, tert-butyl hypochlorite, diiodine, 1,3-diiodo-5,5-dimethylhydantoin, TEMPO

ID: J66-Y2013