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

HRID 326325Notes

Reaction equation

HRID 326325 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.O[O:18][S:19]([O-:21])=O.[K+].[OH2:23]>CO>[CH2:1]([CH:8]([CH2:12][S:19]([C:2]([CH3:7])([CH3:3])[CH3:1])(=[O:21])=[O:18])[C:9]([OH:11])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 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 oxone 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) 1H NMR: 300 MHz spectrum consistent with proposed structure

Sources & evidence

ORD record
ord-eba5979a4485432ca610590ccf9ee06f
Source dataset
uspto-grants-1993_12
Patent number
US05268391

Reaction notes

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