Sulfuric Acid → (4-Phenoxyphenyl)methanol

Participants

Reaction Steps

A solution of sodium borohydride (2.20 g, 58.3 mmol) and concentrated sulfuric acid in diethyl ether (1.6 mL) was added to a solution of 4-phenoxybenzoic acid (5.0 g, 23.3 mmol) in tetrahydrofuran (20 mL) that had been cooled on an ice bath, and the solution was stirred for 4 hours at room temperature. The reaction solution was cooled on an ice bath, methanol was added, then, the solution was allowed to room temperature and stirred for 30 minutes. This reaction solution was cooled again, ethyl acetate and an aqueous solution of 2N sodium hydroxide were added for partitioning, the organic layer was washed with 10% sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 4-phenoxybenzyl alcohol (4.669, quantitatively) as a colorless solid. This 4-phenoxybenzyl alcohol was used to carry out an analogous reaction to Preparation Example 2, and the title compound (886 mg) was obtained as a pale brown solid.

Provenance & Evidence