Acetic Anhydride → HCID 67374420, compound

Participants

Reaction Steps

To a stirred suspension of 2-hydroxy-5-iodo-3-methylbenzoate (1.24 g, 4.25 mmol) in neat acetic anhydride (1.803 mL, 19.10 mmol) was added a 3 drops of concentrated sulfuric acid (0.226 mL, 4.25 mmol). The resultant orange solution was stirred at room temperature overnight. The solution was diluted with 3% aqueous NaHCO3 (13 mL) and extracted with CHCl3 (3×30 mL). The combined organic phases were washed with water (4×20 mL), dried (MgSO4), and concentrated in vacuo to afford methyl 2-(acetyloxy)-5-iodo-3-methylbenzoate, as a colorless solid. 1H NMR (500 MHz, CHCl3): δ 8.17 (s, 1 H); 7.78 (s, 1 H); 3.89 (s, 3 H); 2.25 (s, 3 H); 2.21 (s, 3 H).

Provenance & Evidence