Nitric Acid → 4-Acetoxy-3,5-dimethoxy-2-nitrobenzoic Acid

Participants

Reaction Steps

Fuming nitric acid (5.2 mL) was added, carefully, to a solution of o-acetylsyringic acid 82 (11.1 g, 46.2 mmol) in acetic anhydride (33 g, mmol) at 5° C. and the reaction mixture was then allowed to stir for 3 hours at room temperature. The reaction mixture was poured over ice (300 mL) and the yellow precipitate was collected by filtration, washed with water (3×100 mL) and dried in vacuo to afford the product as a pale yellow solid (12.4 g). H1NMR (270 MHz, CDCl3) δ 7.37 (s, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 2.39 (s, 3H).

Provenance & Evidence