Thioglycolic Acid → 4-(4-Methylphenylsulfonyl)phenylthio acetic acid

HRID 2392

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14](Cl)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C[SH:20].[OH-].[K+].[CH3:25][CH:26]([OH:28])C>CN(C)C=O.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:25][C:26]([OH:28])=[S:20])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

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.

Workup

filtrationfiltered off
customto obtain a precipitate
customAfter the precipitate obtained
filtrationthe insoluble matter was filtered off
addition150 ml of concentrated chloric acid and 500 g of ice were added
filtrationThe formed white crystal was filtered off
washwashed with water
customfurther recrystallized with a mixed solvent of n-hexane and ethylacetate

Sources & evidence

ORD record: ord-ceb80269f1a342758c971e5e753be1b3
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728879

Linked notes

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