4-(Chloromethyl)tolunitrile

1592-20-7

874-86-2

General procedure for the synthesis of p-cyanobenzyl chloride from 4-chloromethylstyrene: 0.4 mmol of 4-chloromethylstyrene, 2 mmol of sodium nitrite, 5 mg of metal iron(III) porphyrin catalyst, and 4.5 mL of acetonitrile solvent were added to the reaction tube. The mixture was heated to 70 °C under air atmosphere and stirred. 0.5 mL of formic acid was added slowly and dropwise over the first 0.5 hr of the start of the reaction. After the reaction lasted for 4 hours, the heating and stirring was stopped and the reaction mixture was cooled to room temperature. The solvent was removed using a rotary evaporator to obtain the crude product. The crude product was purified by column chromatography and the eluent was a solvent mixture of petroleum ether and ethyl acetate. The final target product, p-chloromethylbenzonitrile, was obtained as a white solid in 96.2% yield. The NMR data are shown below.