Nitric Acid → HCID 18968198, compound

Participants

Reaction Conditions

Reaction Steps

A 3-necked round-bottomed flask was charged with conc. HNO3 (240 ml) and cooled to 10° C. with the aid of an ice/acetone bath. Conc. H2SO4 (240 ml) was then added slowly so as to maintain the temperature below 30° C. 2-Phenylbutyronitrile (Aldrich, 110 ml) was introduced dropwise to the stirred solution over a period of 1 hour, maintaining the temperature below 20° C. The ice/acetone bath was then removed and the mixture stirred for a further 30 minutes at ambient temperature before pouring it onto crushed ice (100 g). The resulting mixture was extracted with ethyl acetate (1500 ml×2) and the extracts pooled, washed with saturated bicarb. (1000 ml) and water (500 ml). After drying over MgSO, the ethyl acetate was evaporated under reduced pressure to give crude 2-(4-nitrophenyl)butyronitrile as a yellow oil, crude yield 138 g, 98%. Analysis by GC.MS indicated a para:meta ratio of 3.5:1.

Provenance & Evidence