Methanol → Methyl 5-iodo-2,4-dimethylbenzoate

Participants

Reaction Conditions

Reaction Steps

5-Iodo-2,4-dimethylbenzoic acid (2.78 g, 10.1 mmol) obtained in Step 1 of Example 1-1 was placed in a reaction vessel, and then methanol (20 ml) was added thereto. The resulting mixture was cooled to 0° C. Thionyl chloride (2.2 ml, 30.1 mmol) was added dropwise to the mixture over about 10 minutes. The resulting mixture was stirred under reflux for 3 hours. The reaction solution was distilled off under reduced pressure. A saturated aqueous sodium bicarbonate solution was added to the obtained residue. The solution was extracted twice with ethyl acetate. The organic layers were combined together, and washed with a saturated aqueous sodium chloride solution. Then, the organic solution was dried over anhydrous magnesium sulfate. After removal of anhydrous magnesium sulfate by filtration, the liquid was washed with ethyl acetate. The filtrate and washing solution were combined together, and ethyl acetate was distilled off under reduced pressure to yield 2.85 g (97%) of 5-iodo-2,4-dimethylbenzoic acid methyl ester.

Provenance & Evidence