Hydrochloric Acid → 4-(3-Benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde

Participants

Reaction Steps

To a solution of 4-(3-benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde (3.3 g, 8.8 mmol) in THF (50 mL) was added 6M HCl (6 mL) and the solution refluxed for 2 hours. The volatile organics were removed in vacuo and the aqueous residue extracted with EtOAc (2×25 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hex:EtOAc 70:30) to give 4-(3-benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde (2.5 g, 85%). 1H NMR (400 MHz, CDCl3): δ 10.13 (s, 1H), 7.43-7.25 (m, 6H), 6.85 (d, J=8.4 Hz, 1H), 6.68 (d, J=13.2 Hz, 2H), 6.34 (s, 1H), 6.24 (s, 1H), 5.04 (s, 2H), 2.52 (s, 3H). MS (ESI) m/z=335 [M+H]+.

Provenance & Evidence