2-Phenoxybenzoic acid → 2-Phenoxybenzyl alcohol

Participants

Reaction Steps

To a solution of o-phenoxybenzoic acid (19.0 g, 88.7 mmol) in THF (100 mL) at 0° C. under N2 was added BH3.THF (133 mL, 1.0M in THF) over a period of 1 h, keeping the temperature below 5° C. The reaction mixture was then stirred at room temperature for 2 h. It was quenched with H2O, then 1N aqueous HCl. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic mixture was washed with brine, dried over MgSO, and concentrated to a light yellow oil (16.9 g). The crude product was used in the next step without further purification. MS m/e 183.1, [M+H-H2O]+ ; 1H NMR (300 MHz, CDCl3): δ 2.08 (t, 1H, OH), 4.76 (d, 2H, CH2Ar), 6.82-7.48 (m, 9H, ArH). ##STR64##

Provenance & Evidence