Water → 5-Benzyloxy-2-hydroxymethylphenol

Participants

Reaction Steps

To a solution of the benzaldehyde G3a (127.5 g, 0.52 mol) in MeOH (1 L) at 0 ° C., NaBH4 (16 g, 0.42 mol) was added. The reaction mixture was stirred for 18 h at rt. Reaction progress was monitored by TLC. Upon completion, the reaction mixture was reduced to one-fourth volume and was treated with 0.5 N aq H2SO4 to adjust pH to about 6-7 followed by addition of H2O (1 L). Upon vigorous stirring white precipitate formed. After filtration, the precipitate was lyophilized, washed using chilled toluene (ca. −50° C.) and dried under vacuum to obtain G3 (89 g, 0.38 mol, 73%) as an off-white solid: mp 86-88° C. (Lit.8 88-90° C.); 1H NMR (DMSO, 400 MHz) δ 9.33 (1H, s), 7.35 (5H, m,) 7.08 (1H, d, J=8.4 Hz), 6.42 (2H, m), 5.01 (2H, s), 4.80 (1H, m), 4.39 (2H, s).

Provenance & Evidence