Conversion of Aldoximes into Nitriles with Raney Nickel in Refluxing 2-Propanol

Abstract

Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol.

Keywords:

• Dehydration of aldoximes
• nitrile preparation
• Raney nickel

ACKNOWLEDGMENTS

D. R. Z. gratefully acknowledges financial support a National Science Foundation/Research Site for Educators in Chemistry grant (CHE-9974734) and a Covenant College research grant. R. C. M. gratefully acknowledges financial support from the Research Corporation, the University of Chattanooga Foundation, and the Grote Chemistry Fund. In addition, we are indebted to W. R. Grace Company, Chattanooga, Tennessee, for the generous donation of Raney catalysts.

Notes

^a Time to reach complete conversion as determined by GC.

^b Isolated yields. Product nitriles were compared to authentic spectra or literature reference spectra and confirmed by ¹H NMR and ¹³C NMR spectroscopy and GC-MS.

^c Substrate/Raney nickel, 1/2.5 (w/w).

^d Substrate/Raney nickel, 1/5 (w/w).

^e Substrate/Raney nickel, 1/7.5 (w/w).

^f Product loss observed during rotary evaporation due to volatility of nitrile.