4-Chlorobenzenesulfonyl chloride → Sodium 4-chlorobenzenesulfinate

Participants

Reaction Steps

To a mixture of 504 g of sodium sulfite and 1.8 l of water was added portionwise 16 g of p-chlorobenzenesulfonyl chloride at 50° C. After being stirred at 55°-60° C. for 3 hours, the mixture was cooled with ice and white crystals which separated out were collected and washed with cold water to obtain 152 g of sodium p-chlorobenzenesulfinate. In a manner similar to Synthesis Example 1, sodium p-chlorobenzenesulfinate and ethyl chloroacetate were reacted to obtain ethyl p-chlorophenylsulfonyl acetate. The ester thus obtained (110 g) was added portionwise to a 20% sodium hydroxide aqueous solution while cooling with ice. During this procedure, white crystals separated out quickly. After stirring at room temperature for 1 hour, the mixture was cooled with ice and white crystals were collected by filtration and washed with isopropanol. The crystals thus obtained were dissolved in 300 ml of water and the solution was neutralized with diluted hydrochloric acid. The white crystals which separated out were collected by filtration, washed with water to obtain 90 g of p-chlorophenylsulfonylacetic acid.

Provenance & Evidence