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

Participants

Reaction Steps

To a solution of 5-benzyloxy-2-hydroxymethylphenol (2.39 g, 10.4 mmol) in CH2Cl2 (52 mL) and MeOH (5 mL) is added MnO2 (9.05 g, 104 mmol). The suspension is stirred at ambient temperature overnight. The mixture is filtered and the solvent removed under reduced pressure. The crude material is purified by flash chromatography using CH2Cl2 to afford 4-benzyloxy-2-hydroxybenzaldehyde as a pale yellow solid: 1H NMR (CDCl3) δ 11.45 (s, 1H), 9.70 (s, 1H), 7.43-7.39 (m, 6H), 6.59 (dd, J=2.28 Hz), 6.50 (d, J=2.27 Hz, 1H), 5.10 (s, 2H); (M+H)+=229.

Provenance & Evidence