Hydrogen Peroxide → 4-(1-Butyl)-4-hydroxy-1-(4-methoxyphenyl)-2-phenyl-3,5-pyrazolidinedione

HRID 23571Notes

Reaction equation

HRID 23571 reaction equation
[CH2:1]([CH:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].[OH:26]O.[OH-].[Na+]>CO>[CH2:1]([C:5]1([OH:26])[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 225750444-(1-Butyl)-1-(4-methoxyphenyl)-2-phenyl-3,5-pyrazolidinedione

Product 1

HCID 99065934-(1-Butyl)-4-hydroxy-1-(4-methoxyphenyl)-2-phenyl-3,5-pyrazolidinedione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from 4-(1-butyl)-1-(4-methoxyphenyl)-2-phenyl-3,5-pyrazolidinedione (1.35 g; 3.8 mmol), 35% H2O2 (4.3 ml; 50 mmol), 2 M NaOH (0.35 ml; 0.7 mmol), and methanol (50 ml) using the procedure of Example 7. Purified by flash chromatography on a 110×65 mm silica gel 60 column eluted with ethyl acetate-heptane (1:1) to give 0.7 g (52%).

Workup

  1. customPurified by flash chromatography on a 110×65 mm silica gel 60 column
  2. washeluted with ethyl acetate-heptane (1:1)
  3. customto give 0.7 g (52%)

Sources & evidence

ORD record
ord-920cc9432f7e4718b74617edfcaeea87
Source dataset
uspto-grants-2005_02
Patent number
US06852749B1

Reaction notes

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