Hydrochloric Acid → 2-Ethyl-4,6-dihydroxybenzaldehyde

Participants

Reaction Steps

To a suspension of 5-ethyl-benzene-1,3-diol (2.17 g, 15.72 mmol) and triethyl orthoformate (23.26 g, 157 mmol) in benzene (40 mL) was added AlCl3 (6.30 g, 47.16 mmol) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes. After cooling to room temperature, the mixture was poured onto ice and acidified with HCl. The mixture was extracted with EtOAc and the organic extracts was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2-ethyl-4,6-dihydroxy-benzaldehyde (1.0 g, 38%). 1H NMR (400 MHz, CDCl3δ 12.40 (s, 1H), 10.08 (s, 1H), 6.25 (s, 1H), 6.00 (s, 1H), 5.80 (s, 1H), 2.90 (m, 2H), 1.30 (m, 3H).

Provenance & Evidence