Hydrogen Peroxide → 2,6-Di-t-butyl-p-benzoquinone

HRID 985748Notes

Reaction equation

HRID 985748 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH:16]O>C(O)(=O)C>[C:11]([C:7]1[C:6](=[O:15])[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9](=[O:16])[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 128672,6-Di-t-butyl-p-benzoquinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2,6-di-t-butylphenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20% w/w) in acetic acid (5 ml) was heated with stirring at 50-60° C. under inert atmosphere. To this reaction mixture was added aq. 30% H2O2 (20 mmol) drop wise over 15 min. and heated for 3 h. The catalyst was recovered by simple filtration and 2,6-di-tert-butyl-1,4-benzoquinone formed (65%) was separated by chromatographic purification.

Workup

  1. temperaturewas heated
  2. temperatureheated for 3 h
  3. filtrationThe catalyst was recovered by simple filtration and 2,6-di-tert-butyl-1,4-benzoquinone
  4. customformed (65%)
  5. customwas separated by chromatographic purification

Sources & evidence

ORD record
ord-916bef52782443e3972b889666b65915
Source dataset
uspto-grants-2005_03
Patent number
US06872857B1

Reaction notes

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