Phenol → 2-(Hexafluoro-2-hydroxy-2-propyl)phenol

Participants

Reaction Conditions

Reaction Steps

94.11 g (1000 mmol) of phenol and 166.02 g (100 mmol) of AlCl3 were initially charged in 1200 ml of 1,2-dichloroethane and cooled to −35° C. At this temperature, the precalculated amount of 166.02 g (1000 mmol) of hexafluoroacetone was metered in from a bomb. Subsequently, the reaction mixture was allowed to come to room temperature (20° C., RT) and stirred at RT for a further 36 h. The reaction flask was subsequently flushed with N2 and the offgas passed into a wash bottle containing water. For workup of the remaining reaction solution, 500 ml of water were added cautiously and the mixture was stirred well. Subsequently, the organic phase was removed, the aqueous phase was extracted with CH2Cl2 and dried over magnesium sulphate, and the solvent was removed on a rotary evaporator. As this was done, the residue crystallized out. For purification, the resulting crystals were slurried in n-hexane and filtered off, and 230 g (842 mmol, yield: 82.4% of theory) of a white, crystalline solid were obtained.

Provenance & Evidence