[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:7][CH2:8][CH2:9][C:10]#[N:11])([O-:14])=[O:13]4-Phenylbutyronitrile (12.7 g) was added dropwise to stirred concentrated nitric acid (55 ml) at 5°-10° C. and the mixture was stirred for 2 hours at 20°-25° C. The deep yellow solution was poured onto ice and extracted with dichloromethane. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:4) to isolate the minor product.
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