Acetic Anhydride → 3,4,5-Trimethoxyphenyl acetate

Participants

Reaction Steps

A solution of 3,4,5-trimethoxyphenol (5.52 g, 30 mmol) in acetic anhydride (15 mL) was refluxed for 4 h. The reaction mixture was poured onto crushed ice (50 g). The resulting precipitate was collected and washed with water. The residue was dried in vacuum at 50° C. for 24 h to afford white crystals (6.31 g, 93%), 74-75° C.; 1H NMR (CDCl3, 200 M Hz) δ 6.34 (s, 2H), 3.83 (s, 6H), 3.82 (s, 3H), 2.29 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 169.6 (s), 153.5 (s, 2C), 146.7 (s), 135.8 (s), 99.1 (d, 2C), 60.9 (q), 56.1 (q, 2C), 21.1 (q).

Provenance & Evidence