Hydrochloric Acid → 1-(4-Bromophenyl)-2-hydroxy-2-p-tolylethanone

Participants

Reaction Steps

A solution of 67 g. (0.314 mole) of p-bromophenylglyoxal in 300 ml. of dry toluene is added dropwise over 1 1/2 hours to a stirrred suspension of 84 g. (0.6 mole) of anhydrous aluminum chloride in 1.25 1. of dry toluene cooled in an ice-bath. Stirring in the cold is continued for 5 hours and the mixture then is held at 5°-10° C. overnight. The mixture is poured into about 2 1. of ice and 6N hydrochloric acid. The aqueous phase is separated and re-extracted with three portions of benzene. The combined, washed and dried organic extracts are concentrated under reduced pressure to a volume of about 200 ml. Dilution with 150 ml. of petroleum ether precipitates the white crystalline product, m.p. 80°-82° C. Repeated recrystallization from 60% ethanol affords the analytical sample, m.p. 82°-83.5° C.

Provenance & Evidence