Phenol → 2-Hydroxybenzonitrile

Participants

Reaction Steps

To a solution of 1.13 ml of boron tribromide in 6 ml of 1,2-dichloroethane were added a solution of 941 mg of phenol in 10 ml of 1,2-dichloroethane, 0.82 ml of methyl thiocyanate and 1.33 g of aluminium chloride under ice-cooling. After dissolving aluminium chloride with stirring at room temperature, the mixture was heated at 80° C. on an oil bath for 3 hr. After cooling, the reaction solution was poured into 33 ml of 4N aqueous sodium hydroxide and stirred at 75°-80° C. for 30 min. on an oil bath. After washing with methylene chloride, the aqueous layer was acidified with 25 ml of 6N HCl and extracted with ether. The ether layer was extracted with 2N aqueous sodium carbonate, dried over anhydrous magnesium sulfate and concentrated to recover 147 mg of phenol. On the other hand, the sodium carbonate layer was acidified with 6N HCl, extracted with ether, and the ether layer was dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from methylene chloride-petroleum ether to give 943 mg of 2-cyanophenol as white crystals melting at 97°-98° C.

Provenance & Evidence