Reaction #2488

Reaction equation

2-propanol

4-methyl-4'-chlorodiphenylsulfone

thioglycolic acid

potassium hydroxide

→

4-(4-methylphenylsulfonyl)phenylthio acetic acid

Solvents

water

N,N-dimethylformamide

Conditions

Workup

1. 1
   Filtrationfiltered off
2. 2
   Otherto obtain a precipitate
3. 3
   OtherAfter the precipitate obtained
4. 4
   Filtrationthe insoluble matter was filtered off
5. 5
   workup.ADDITION150 ml of concentrated chloric acid and 500 g of ice were added
6. 6
   FiltrationThe formed white crystal was filtered off
7. 7
   Washwashed with water
8. 8
   Otherfurther recrystallized with a mixed solvent of n-hexane and ethylacetate

Procedure

In 250 ml of N,N-dimethylformamide, 140 g of 4-methyl-4'-chlorodiphenylsulfone was dissolved, and further 77 g of thioglycolic acid and 71 g of 85% potassium hydroxide pellet were added and stirred for 6 hours at 120° C. The reaction mixture was poured into 2-propanol and filtered off to obtain a precipitate. After the precipitate obtained was dissolved in water and then the insoluble matter was filtered off, 150 ml of concentrated chloric acid and 500 g of ice were added therein. The formed white crystal was filtered off and washed with water and further recrystallized with a mixed solvent of n-hexane and ethylacetate to obtain 110 g of the intended 4-(4-methylphenylsulfonyl)phenylthio acetic acid.

Source