Veratrole → HCID 21584605, compound

Participants

Reaction Steps

2',6',3,4-Tetramethoxybenzophenone was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone except using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.47 g, 11 mmol) and 2,6-dimethoxybenzoyl chloride (2.0 mL, 10 mmol) with a reaction time of 24 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride) to afford 2.11 g (70%) of the product as a white solid: mp 128-129° C.; 1H NMR (CDCl3) δ 7.66-7.60 (m, 1H), 7.40-7.20 (m, 2H), 6.88-6.79 (m, 1H), 6.67-6.65 (m, 2H), 3.93 (s, 3H), 3.91 (s, 3H), 3.71 (s, 6H); 13C NMR (CDCl3) δ 193.8, 157.4, 153.4, 148.9, 130.9, 130.5, 125.3, 118.0, 110.2, 109.9, 104.0, 55.9, 55.8; Anal. Calcd for C17H18O5. Theoretical: C, 67.54; H, 6.00. Found: C, 66.51; H, 5.91.

Provenance & Evidence