Hydrogen Peroxide → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

HRID 1979665Notes

Reaction equation

HRID 1979665 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[OH:11]O>C(O)(=O)C>[CH3:9][C:4]1[C:3](=[O:10])[C:2]([CH3:1])=[C:7]([CH3:8])[C:6](=[O:11])[CH:5]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 170162,3,6-Trimethylphenol

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

500 mg of 2,3,6-trimethylphenol and 30 mg of the catalyst prepared in Example 6 were added to 5 ml of acetic acid, and 1 g of a 30% hydrogen peroxide aqueous solution was further added at room temperature. The mixture was stirred for 6 hours. After the completion of the reaction, the catalyst was removed by filtration, and the acetic acid solution was washed with an aqueous solution of NaHCO3 and extracted with ether. After drying over MgSO4, the solution was concentrated, and the residue was eluted through a silica gel column with dichloromethane, whereby 515 mg (94% yield) of trimethylbenzoquinone was obtained. The physical properties of the product (yellow needle-like crystals as crystallized from hexane, having a melting point of 28° C.) corresponded to the values identified in the literature [Org. Syn. 52, 83 (1972].

Workup

  1. additionwas further added at room temperature
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed by filtration
  4. washthe acetic acid solution was washed with an aqueous solution of NaHCO3
  5. extractionextracted with ether
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe solution was concentrated
  8. washthe residue was eluted through a silica gel column with dichloromethane

Sources & evidence

ORD record
ord-b7bfd4c099404bf3a43d41db9dac0d35
Source dataset
uspto-grants-1984_11
Patent number
US04482493

Reaction notes

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