Water → [4-(Benzenesulfonyl)phenyl]phenylphosphinic acid

Participants

Reaction Steps

4-(phenylsulfonyl)benzene diazonium tetrafluoroborate was prepared from 4-aminophenyl phenyl sulfone according to the method of example 11. A slurry of 44 grams of the 4-(phenylsulfonyl)benzenediazonium tetrafluoroborate, 22.8 ml of dichlorophenylphosphine, and 0.5 grams of copper (I) chloride in 400 ml. of ethyl acetate was heated at 30° C for 1.5 hours, cooled, and decomposed by adding 125 ml. of water. The ethyl acetate was removed by steam distillation, and the solid was collected by filtration of the aqueous residue. This solid was extracted with 2 liter of 10% sodium hydroxide, and the extract was acidified with hydrochloric acid to give crude acid. Crystallization from 80% ethanol gave 20 grams (45% yield) of phenyl[4-(phenylsulfonyl)phenyl]phosphinic acid, m.p. 225°-228° C.

Provenance & Evidence