Water → (1,1'-Biphenyl)-2,3'-diol

Participants

Reaction Steps

A 2.5 liter sulfonation flask fitted with thermometer, stirrer, condenser and nitrogen inlet is charged with 153 g (0.39 g mol) of 2,6-bis(4-methoxybenzoyl)naphthalene in 1350 ml of toluene and, with stirring, 282.7 g (2.12 mol) of aluminium chloride are added in portions over 15 minutes at 8° C. The reaction mixture is stirred for 4 hours at 75° C., then cooled to room temperature, and charged into 10 liters of water with vigorous stirring. The resultant suspension is filtered and the residue is vacuum dried at 130° C., giving 142.4 g (99.9% of theory) of a brownish powder which melts at 307° C. 67 g of the crude product are dissolved warm in 320.1 g 5% aqueous sodium hydroxide, and the solution is dried over Hyflo (filter aid based on diatomaceous earth (kieselguhr)) and the clear filtrate is charged to 2 liters of water containing 39.5 g of 37% of hydrochloric acid. The precipitated product is filtered, washed with water and vacuum dried at 130° C., giving 62.3 g (92.8% of theory) of the desired diphenol. The product melts at 307° C.

Provenance & Evidence