Water → 2-Benzyl-3-(tert-butylsulfonyl)propanoic acid

HRID 6082Notes

Reaction equation

HRID 6082 reaction equation
[CH2:1]([CH:8]([CH2:12]C(C)(C)C)[C:9]([OH:11])=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17]([O-:22])(O[O-])(=O)=[O:18].[K+].[K+].[OH2:25]>CO>[CH2:1]([CH:8]([CH2:12][S:17]([C:2]([CH3:7])([CH3:3])[CH3:1])(=[O:22])=[O:18])[C:9]([OH:11])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 10313463Potassium peroxymonosulphateHCID 178418656HCID 178418656, compound

Product 1

HCID 141580582-Benzyl-3-(tert-butylsulfonyl)propanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

280 mg of 2-benzyl-3-tert.-butylthiopropionic acid was dissolved in 5 ml of methanol and, while cooling with ice, 1 g of potassium peroxomonosulfate in 4 ml of water was added and the whole was stirred overnight at room temperature. The solution was diluted with water and extracted with methylene chloride, and the extracts were dried and concentrated by evaporation (260 mg, 82% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal. calcd. for C14H20O4S: C, 59.13; H, 7.09. Found: C, 59.39; H, 7.08.

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride
  3. customthe extracts were dried
  4. concentrationconcentrated by evaporation (260 mg, 82% yield)

Sources & evidence

ORD record
ord-aa19428af98a44e881b7ee2b0e2130c2
Source dataset
uspto-grants-1993_09
Patent number
US05246969

Reaction notes

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