styrylsulfonylacetic acid → HCID 5463590, compound

HRID 278137Notes

Reaction equation

HRID 278137 reaction equation
C(CC(O)=S)=CC1C=CC=CC=1.[CH:13]([S:21]([CH2:24][C:25]([OH:27])=[O:26])(=[O:23])=[O:22])=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C.OO>[CH:13](/[S:21]([CH2:24][C:25]([OH:27])=[O:26])(=[O:22])=[O:23])=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 523014styrylsulfonylacetic acidHCID 178526177HCID 178526177, compound2×

Product 1

HCID 5463590HCID 5463590, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 784Hydrogen PeroxideSolvent

Procedure

The styrylthioacetic acid is then oxidized to styrylsulfonylacetic acid as follows. A mixture of styrylthioacetic acid (5 g, 25 mmol) in glacial acetic acid (35 ml) and 30% hydrogen peroxide (15 ml) is heated under reflux for 60 minutes and the mixture is poured onto crushed ice (200 ml) after cooling. The compound separated is filtered and recrystallized from hot water to give white crystalline flakes of (Z)-styrylsulfonylacetic acid; yield 2.4 g (41%); m.p. 150-51 ° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 60 minutes
  3. additionthe mixture is poured
  4. temperatureafter cooling
  5. customThe compound separated
  6. filtrationis filtered
  7. customrecrystallized from hot water

Sources & evidence

ORD record
ord-62a4bf87a7d3460391ccb5680733d59c
Source dataset
uspto-grants-2002_03
Patent number
US06359013B1

Reaction notes

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