Hydrogen Peroxide → 1,2-Diphenyl-4-hydroxy-4-(4-methylphenyl)-3,5-pyrazolidinedione

HRID 23572

Reaction equation

HRID 23572 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH:10]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[C:9](=[O:20])[N:8]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.S(S([O-])=O)([O-])(=O)=[O:30].[Na+].[Na+]>C(O)(=O)C>[C:1]1([N:7]2[C:11](=[O:12])[C:10]([OH:30])([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[C:9](=[O:20])[N:8]2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 656671Sodium PyrosulfiteHCID 225750461,2-Diphenyl-4-(4-methylphenyl)-3,5-pyrazolidinedione

Product 1

HCID 97988671,2-Diphenyl-4-hydroxy-4-(4-methylphenyl)-3,5-pyrazolidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,2-diphenyl-4-(4-methylphenyl)-3,5-pyrazolidinedione (1.10 g; 3.2 =mol), 35% H2O2 (0.47 ml; 5.5 mmol), and acetic acid (40 ml) was stirred 16 days at room temperature. Sodium metabisulfite (1.0 g) was added and excess acetic acid evaporated off. The residue was dissolved in hot ethyl acetate (25 ml) and benzene (25 ml) and filtered. After cooling to room temperature, the mixture was filtered and the residue recrystallized from 50% aqueous ethanol (20 ml) to give 0.58 g (53%).

Workup

  1. customexcess acetic acid evaporated off
  2. dissolutionThe residue was dissolved in hot ethyl acetate (25 ml)
  3. filtrationbenzene (25 ml) and filtered
  4. temperatureAfter cooling to room temperature
  5. filtrationthe mixture was filtered
  6. customthe residue recrystallized from 50% aqueous ethanol (20 ml)
  7. customto give 0.58 g (53%)

Sources & evidence

ORD record
ord-baeea72672b647a4baeb6e9fbd6b854b
Source dataset
uspto-grants-2005_02
Patent number
US06852749B1

Linked notes

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