styrylsulfonylacetic acid → HCID 5463590, compound

HRID 1266473Notes

Reaction equation

HRID 1266473 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-681da380de55444b8418a6ab99bb57b3
Source dataset
uspto-grants-2003_04
Patent number
US06548553B2

Reaction notes

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