Ammonia → 2-Hydroxy-4-methoxybenzophenone

Participants

Reaction Steps

214 g ( =1.0 mole) of 2,4-dihydroxybenzophenone were added to a mixture of 500 ml of 2 N sodium hydroxide solution and 150 ml of water at room temperature and stirring was carried out until everything had dissolved (20 minutes). Thereafter, 31.6 ml (=0.33 mole) of dimethyl sulfate were added and stirring was continued for 0.5 hour, after which a further 31.6 ml (=0.33 mole) of dimethyl sulfate were added while stirring. After 0.5 hour, a further 31.6 ml (=0.33 mole) of dimethyl sulfate were added while stirring and, after 0.5 hour, 50 ml of 2 N sodium hydroxide solution and 9.5 ml of dimethyl sulfate were added. The mixture was stirred for 1 hour at room temperature, 30 ml of concentrated ammonia solution were added and stirring was then continued for a further 0.5 hour. The precipitate which had separated out was filtered off under suction and washed with a little water to give 349 g (202.4 g of dry product=89% of theory) of moist 2-hydroxy-4-methoxybenzophenone, which contains 1.07% of 2,4-dimethoxybenzophenone. The moist filtration residue was recrystallized from 1,170 ml of methanol with the addition of 5 g of active carbon. After filtration under suction and drying under reduced pressure from a water pump at 50° C., 171 g (=75% of theory) of pure 2-hydroxy-4-methoxybenzophenone of melting point 62°-63° C. were obtained. According to gas chromatography, the product did not contain any dimethoxy derivative.

Provenance & Evidence