Hydrochloric Acid → 3,3,3-Triphenylpropan-1-ol

Participants

Reaction Steps

Borane-methyl sulfide (60 mL, 0.63 mol) was added dropwise to 100 g (0.33 mol) of 3,3,3-triphenylpropanoic acid and 38 mL (0.33 mol) trimethyl borate in 1 liter of anhydrous tetrahydrofuran at room temperature. After 18 hr, the reaction mixture was carefully acidified with 180 mL of conc. hydrochloric acid, stirred for 3 hours and then further diluted with ca. 450 mL of water. The THF layer was collected, the aqueous layer extracted twice with dichloromethane, and the organic layers combined and dried over magnesium sulfate. The organic solution was evaporated to leave a solid, which was recrystallized (two crops) from hexane-dichloromethane to give 83.3 g (87.5%) of the title compound, mp 103°-106° C.

Provenance & Evidence