Hydrogen Peroxide → 2-[[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]sulfinyl]-2-methylpropionic acid

HRID 745988Notes

Reaction equation

HRID 745988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([S:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH:24]O>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([S:17]([C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])=[O:24])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 140125362-[[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]thio]-2-methylpropionic acid

Product 1

HCID 136560912-[[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]sulfinyl]-2-methylpropionic acidYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

5.56 g (16.0 mmol) of 2-[[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]thio]-2-methylpropionic acid and 6 ml of 30% H2O2 were combined in 200 ml glacial acetic acid. The mixture was stirred at room temperature and monitored by TLC for the disappearance of starting material and the appearance of product. After about four hours the reaction was stopped by diluting with excess 3N HCl. The resulting precipitate was filtered and washed several times with cold toluene to yield white crystals, 3.38 g (58%) of 2-[[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]sulfinyl]-2-methylpropionic acid, m.p. 184°-185° C.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed several times with cold toluene

Sources & evidence

ORD record
ord-64a897c576b4455899f8b587f161f1d8
Source dataset
uspto-grants-1986_07
Patent number
US04602028

Reaction notes

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