Veratrole → 2-(3,4-Dimethoxybenzoyl)furan

Participants

Reaction Steps

2-(3,4-Dimethoxybenzoyl)furane was prepared analogously to 3,4,3′,4′-tetramethoxybenzophenone using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.5 g, 10 mmol) and 2-furoyl chloride (1.1 mL, 10 mmol) with a reaction time of 2 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride) to afford 1.69 g (78%) of the product as a white solid: mp 112–114° C.; 1H NMR (CDCl3) δ 7.78–7.66 (m, 2H), 7.59–7.52 (m, 1H), 7.26–7.17 (m, 1H), 6.96–6.90(m, 1H), 6.63–6.55 (m, 1H), 3.97 (s, 3H), 3.96 (s, 3H); 13C NMR (CDCl3) δ 180.9, 153.0, 152.5, 148.9, 146.5, 129.8, 124.0, 119.6, 112.0, 111.7, 110.0, 56.0, 55.9; Anal. Calcd for C13H12O4. Theoretical: C, 67.23; H, 5.21. Found: C, 67.09; H, 5.21.

Provenance & Evidence