Boron trifluoride etherate → 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

Boron trifluride etherate (13.0 mL) was added dropwise to a solution of 3,4,5-tri-methoxyphenyl acetate 4 (6.78 g, 30 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 70° C. for 2 h. Then the mixture was poured onto crushed ice (80 g). The light brown oil was separated and distilled under reduced pressure to furnish light yellow oil (5.56 g, 82%); 1H NMR (CDCl3, 200 M Hz) δ 13.42 (br s, 1H), 6.23 (s, 3H), 3.82 (s, 3H), 3.99 (s, 3H), 3.88 (s, 3H), 3.79 (s, 3H), 2.65 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 203.3 (s), 161.8 (s), 160.0 (s), 155.2 (s), 134.7 (s), 108.4 (s), 96.0 (d), 60.9 (q, 2C), 56.0 (q), 31.8 (q).

Provenance & Evidence