Iodine → 5-Iodo-2,4-dimethylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

Commercially available 2,4-dimethylbenzoic acid (6.6 g, 44.0 mmol), iodine (12.1 g, 47.8 mmol), and sodium periodate (4.38 g, 22.1 mmol) were placed in a reaction vessel, and acetic acid (60 ml), anhydrous acetic acid (3 ml), and sulfuric acid (0.75 g) were added thereto. The resulting mixture was stirred at 105° C. for 6 hours. The reaction solution was poured into water (300 ml). The resulting insoluble material was isolated by filtration, washed with water (500 ml), and then dissolved in ethyl acetate (400 ml). The obtained solution was washed sequentially with 5% aqueous sodium thiosulfate solution (100 ml) and saturated sodium chloride solution (200 ml). Then, the solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting solid material was recrystallized with a 2:1 mixture of ethanol and water (450 ml) to yield 5-iodo-2,4-dimethylbenzoic acid (9.1 g, 75%) as needle crystals.

Provenance & Evidence