styrylsulfonylacetic acid → HCID 5463590, compound

HRID 433329Notes

Reaction equation

HRID 433329 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 recrystalized 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. customrecrystalized from hot water

Sources & evidence

ORD record
ord-eba5bc2bf806419f81fbc094f2198226
Source dataset
uspto-grants-2003_12
Patent number
US06667346B2

Reaction notes

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