Hydrochloric Acid → [2,2'-Binaphthalen]-6-ol

Participants

Reaction Steps

In a three-necked flask 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 20.6 g of 2-naphthaleneboronic 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 a mixture of toluene and ethyl acetate, the crystals were collected by filtration, washed with toluene and dried at 80° C. under reduced pressure to give 15.6 g of 6-(2-naphthyl)-2-naphthol. The unreacted 6-bromo-2-naphthol was not detected.

Provenance & Evidence