Acetic Acid → 2-Iodo-1-triphenylmethylimidazole-4-carboxylic acid

Participants

Reaction Steps

A suspension of 2-iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole (1.978 g, 4 mmol) in 6N sodium hydroxide (15 mL) was heated at reflux for 4 hours. The resulting suspension was diluted with ethyl acetate (20 mL) and then slightly acidified with acetic acid. The resulting clear solution was extracted three times with ethyl acetate (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated in vacuo. Residual acetic acid was removed under high vacuum to give 2-iodo-1-triphenylmethylimidazole-4-carboxylic acid (1.67 g, 87%) as a white solid, mp 203-205° C.: 1H NMR (CDCl3) δ 7.60 (s, 1H), 7.38-7.20 (m, 9H), 7.18-7.09 (m, 6H).

Provenance & Evidence