Hydrochloric Acid → 2-Iodo-4-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxyanthranilic acid (30.5 g, 0.18 mol), water (274.5 ml), and concentrated HCl (36.6 ml) is heated at 75° C. to effect solution and then is cooled to 0° C. The mixture is then treated with NaNO2 (13.3 g) in water (27.5 ml), followed by potassium iodide (45.75 g) in a water (75 ml)/H2SO4 (10.1 ml) solution. The reaction mixture is heated on a steam bath for 2 hours, then excess iodine is steam distilled. The reaction mixture is then cooled, and the product is collected by filtration and dried in an oven at 75° C. to afford 39.28 g (78.6%) of crude product. The crude product is treated with toluene, the mixture is filtered, and the filtrate is concentrated to afford 26.03 g of 2-iodo-4-methoxybenzoic acid.

Provenance & Evidence