1-Naphthol → 1-Hydroxynaphthalene-2-carbonitrile

Participants

Reaction Steps

To 6 ml of a solution of 2.02M of boron trichloride in 1,2-dichloroethane were added a solution of 1.44 g of α-naphthol in 30 ml of 1,2-dichloroethane, 0.82 ml of methyl thiocyanate and 1.33 g of aluminium chloride under ice-cooling. After stirring at room temperature for 3 hr., the reaction mixture was poured into 33 ml of 4N aqueous NaOH and stirred at 75°-78° C. on an oil bath for 30 min. After cooling the aqueous layer was washed with methylene chloride, acidified with 25 ml of 6N HCl and extracted with ether. After drying the ether layer over anhydrous magnesium sulfate, the solvent was distilled off. The residue (1.51 g) was purified on a column of 30 g of silica gel. Then 1.26 g of the eluate with 10% ethyl acetate-methylene chloride was recrystallized from ether-petroleum ether to give 1.04 g of 2-cyano-1-naphthol as crystals melting at 182°- 183° C.

Provenance & Evidence