Methanol → 110955-49-2

Participants

Reaction Steps

Sodium sulfite (15.3 g, 121.45 mMole), was dissolved in water (100 mL) and while stirring at room temperature, methyl 4-chlorosulfonylbenzoate (3), (19.0 g, 80.97 mMole) was added a little at a time to the solution. Sodium bicarbonate was added simultaneously in small portions keeping the solution at approximately pH 8. As the reaction proceeds, periodic addition of a little methanol from a wash bottle minimizes foaming. A total of 20 g of sodium bicarbonate were needed to complete the reaction. After complete addition of the reagents, the mixture was then stirred at room temperature for about 30 minutes. The mixture was then filtered. The clear solution was acidified with concentrated hydrochloric acid and treated with sufficient solid sodium chloride to precipitate the product. The white solid was filtered off and air-dried to give 12.7 g of methyl 4-sulfinobenzoate.

Provenance & Evidence