Ethyl Acetate → 3-Benzyloxy-5-chlorobenzyl alcohol

Participants

Reaction Steps

To a stirred solution of 3-benzyloxy-5-chlorobenzoic acid, as described above in Step B, (5.0 g, 19 mmol) in dry THF (150 mL) at 0° C., under argon, was added LiAlH4 (29 mL of a 1.0 M solution in THF, 29 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 hours, then EtOAc (1 mL) was added, followed by water (1 mL), then 15% aqueous NaOH (1 mL), then water (3 mL). The resulting mixture was filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica, eluting with hexane—20% EtOAc to yield the desired product as a colorless oil.

Provenance & Evidence