3-Aminophenol → 3-Amino-4'-(M-Aminophenoxy) Benzophenone

Participants

Reaction Conditions

Reaction Steps

A solution of m-aminophenol 25 g (0.23 mol.) in 160 ml of dimethylsulfoxide and 190 ml of toluene was degassed for 30 minutes by bubbling nitrogen. The temperature was raised to 50° C. and 9.16 g (0.23 mol) of sodium hydroxide as 50% aqueous solution was added. The reaction temperature was slowly raised to 110° C. (oil bath 140° C.) and water was distilled off via toluene-water azeotrope. After all the water was distilled off, the toluene was distilled off till the reaction temperature reached 160° C. Reaction mixture was cooled to 80° C. and 3-amino-4'-chlorobenzophenone 53 g (0.23 mol) was added in small portions. After the addition was complete the reaction temperature was raised to 150° C. and maintained for 4 hours. After cooling to room temperature, the reaction mixture was poured into 800 ml of 2% sodium hydroxide and 1% sodium sulfite solution with rapid stirring. The precipitate semi-solid obtained was washed with water and then taken up in 200 ml of chloroform. The chloroform solution was washed twice with water. After drying with magnesium sulfate, chloroform was removed to provide a dark yellow resin like solid 52.3 g (72%), m.p. 48°-52° C.

Provenance & Evidence