The general procedure for the synthesis of 4-(4'-benzonitrile)cyclohexanone from 4-benzamide-cyclohexanone is as follows: to a 50 ml solution of dichloromethane containing 4.8 g (22.1 mmol) of 4-(4-oxocyclohexyl)benzamide, 3.0 ml (24.3 mmol) of pivaloyl chloride and 2.14 ml (26.5 mmol) of pyridine were sequentially added at room temperature. . The reaction mixture was stirred overnight. After completion of the reaction, the reaction solution was diluted with 50 ml of dichloromethane and washed three times with water. The organic phase was separated and dried over anhydrous magnesium sulfate and subsequently concentrated. Purification by fast column chromatography (silica gel as stationary phase and petroleum ether/ethyl acetate 1:1→1:4 as eluent) gave 700 mg (16% yield) of the target product. The structure of the product was confirmed by 1H NMR (CDCl3): δ 7.61 (d, 2H), 7.36 (d, 2H), 3.09 (m, 1H), 2.51 (m, 4H), 2.25 (m, 2H), 1.96 (m, 2H).
