Hydrochloric Acid → 6-Phenylnaphthalen-2-ol

Participants

Reaction Steps

In a three-necked flask were placed 17.9 g of 6-bromo-2-naphthol, 4.6 g of tetrakistriphenylphosphinepalladium and 200 ml of toluene and the mixture was stirred at room temperature. When the solids nearly dissolved, a solution of 9.8 g of phenylboronic acid in 200 ml of ethanol was added and stirred. Thereafter, a solution of 20 g of sodium carbonate in 200 ml of water was added and the mixture was stirred at room temperature 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 to give 22 g of 6-phenyl-2-naphthol. The amount of the unreacted 6-bromo-2-naphthol was 16%.

Provenance & Evidence