Phenol → 3-[1-(4-Hydroxyphenyl)-isopropyl]phenol

Participants

Reaction Steps

A mixture of 1335 grams (14.2 moles) of phenol, 450 ml. of 75% aqueous sulfuric acid and 1800 ml. of toluene was stirred at room temperature while a solution of 450 grams (2.9 moles) of 3-hydroxyphenyldimethylcarbinol in 890 grams (9.5 moles) of phenol and 1800 ml. of toluene was added over three hours. The reaction mixture was stirred at room temperature for four hours and the aqueous layer was separated and discarded. The organic layer was washed twice with water, once with 10% sodium bicarbonate solution and again with water. Toluene and excess phenol were removed by vacuum distillation and the residue was recrystallized from toluene. There was obtained 371 grams (55% of theoretical) of the desired 2-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)propane.

Provenance & Evidence