Dimethylformamide → Methyl 2-(chlorosulfonyl)-4-methoxybenzoate

Participants

Reaction Steps

To 500 ml of thionyl chloride was added portionwise over 1 hour 100 g of the compound of Example 3. The reaction mixture was stirred 0.5 hours, and 5 ml of dimethylformamide was added over 1 hour. The mixture was refluxed overnight. The orange solution was cooled to ambient temperature and concentrated in vacuo to a yellow semisolid. The reaction product was dissolved in 250 ml dichloromethane, and the solution was concentrated in vacuo. The resulting solid was partitioned between ether and water. The organic phase was washed with water, twice with aqeous sodium bicarbonate, dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 47 g of the title compound, m.p. 69°-72° C.

Provenance & Evidence