Hydrochloric Acid → 6-Phenylnaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

In a three-necked flask equipped with a condenser, a thermometer and a stirrer were placed 26.8 g of 6-bromo-2-naphthol, 4.6 g of tetrakistriphenylphosphinepalladium and 100 ml of toluene and the mixture was stirred at 50° C. When the solids nearly dissolved, a solution of 14.6 g of phenylboronic acid in 100 ml of ethanol was added and stirred. When the solutions mixed with each other, a solution of 30 g of sodium carbonate in 100 ml of water was added, the mixture was heated to the reflux temperature and stirred for 1 hour. Upon completion of the reaction, dilute hydrochloric acid was added until the aqueous layer became weakly acidic, the organic layer was recovered and the solvent was distilled off under reduced pressure. The crude product was recrystallized from 50 ml of toluene and the crystals collected by filtration were washed with toluene and dried at 80° C. under reduced pressure to give 11.9 g of 6-phenyl-2-naphthol. The unreacted 6-bromo-2-naphthol was not detected by HPLC.

Provenance & Evidence