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

HRID 2210933Notes

Reaction equation

HRID 2210933 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.-butylthio-propionic 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: 300MHz 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-b0dccfeb53da4fdda3adb3ce8e28276d
Source dataset
uspto-grants-1995_10
Patent number
US05461074

Reaction notes

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