Hydrochloric Acid → HCID 18443682, compound

Participants

Reaction Steps

To a solution of 4-benzyloxy-2-chlorobenzoic acid (788 mg) in tetrahydrofuran (7.9 ml) was added dropwise borane-dimethylsulfide complex (10.0M, 0.6 ml) at room temperature under a nitrogen atmosphere and the mixture was refluxed under heating for 2.5 hr. The reaction mixture was allowed to cool to room temperature, and 1N hydrochloric acid (1.5 ml) was carefully added dropwise. The mixture was stirred for 30 min. To the reaction mixture was added water and the resulting product was extracted 3 times with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 4-benzyloxy-2-chlorobenzyl alcohol (778 mg) as a white powder.

Provenance & Evidence