4-Benzyloxy-2-hydroxybenzaldehyde → 5-Benzyloxy-2-hydroxymethylphenol

Participants

Reaction Conditions

Reaction Steps

To an ice cooled suspension of 4-benzyloxy-2-hydroxy-benzaldehyde (0.228 g, 1 mmol) in 10 mL of methanol was slowly added sodium borohydride (0.038 g, 1 mmol). After addition of sodium borohydride, a clear solution was obtained. The reaction was stirred at 0° C. for 20 minutes followed by stirring at RT for 10 minutes. The solvent was evaporated under vacuum. To this solid residue was carefully added 0.1 N H2SO4 until the pH dropped to 6.5 with vigorous stirring. Additional water (ca. 40 mL) was added with continuous stirring which then caused the product to precipitate. The solid was filtered and copiously washed with water to remove all traces of acid (last wash pH>7). The solid was immediately vacuum dried to obtain 0.175 g (76%) white solid: mp 88-90° C.; TLC, Rf0.29, in hexanes:EtOAc (2:1); 1H NMR (600 MHz, DMSO-d6) δ, 9.36 (s, 1H, Ph-OH), 7.43-7.32 (m, 5H, C6H5), 7.14-7.12 (d, 1H, J=8.4 Hz, Ar—H6), 6.44-6.41 (m, 2H, Ar—H5/Ar—H3), 5.01 (s, 2H, PhCH2), 4.8 (t, 1H, CH2OH), 4.39 (s, 2H, CH2OH); 13C NMR (100 MHz, DMSO-d6) δ 158.0, 155.2, 137.3, 128.5, 128.4, 128.3, 127.6, 127.5, 127.3, 121.2, 104.8, 101.8, 68.9, 57.9; analysis calcd. for C14H14O3. C, 73.03; H, 6.13. found: C, 73.16; H, 5.94.

Provenance & Evidence