Benzyl Alcohol → HCID 19795269, compound

Participants

Reaction Steps

A solution of 75.0 g (0.374 mol) of benzylphenyl sulfide, 60.73 g (0.561 mol) of benzyl alcohol in 350 ml of methylene chloride is introduced into a reaction vessel provided with a stirrer and thermometer. 182.45 g (1.12 mol) of 54% by weight HBF4 in diethyl ether are added dropwise at an internal temperature of 20°-30° C. in the course of 35 min, while stirring. The reaction mixture is then stirred at RT for 2 h. The reaction mixture is diluted with 300-400 ml of methylene chloride and extracted 4 times with water (pH ~6). The organic phase is then dried over MgSO4 and the solvent is removed on a rotary evaporator. The yellow-brown oil which remains is stirred in 400 ml of toluene and the mixture is left to crystallize at 0°-5° C. for about 1 h. The suspension is filtered and the residue is washed with a little cooled toluene (0°-5° C.). The pure product is dried under a high vacuum at RT overnight. 123.8 g (87% of theory) of dibenzylphenylsulfonium tetrafluoroborate are obtained as white crystals of melting point 110°-115° C.

Provenance & Evidence