Hydrogen Peroxide → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-
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>[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:9])=[CH:5][C:6](=[O:11])[C:7]=1[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
500 mg of 2,3,6-trimethylphenol and 10 mg of RuCl3.3H2O were dissolved in 5 ml of acetic acid, and 1 g of 30% hydrogen peroxide was dropwise added to the solution at room temperature. The mixture was stirred for 5 hours. (In some cases, a dimer precipitates in the reaction solution (from 0 to 10%), but it can readily be removed by filtration.) After adding a small amount of a sodium thiosulfate solution, the reaction mixture was extracted with ether. The ether layer was dried over magnesium sulfate and subjected to distillation under reduced pressure to remove the ether. The residue was purified by a silica gel column (by using methylene chloride as the eluent), whereby 496 mg (90% yield) of 2,3,6-trimethylbenzoquinone was obtained. The physical properties of the trimethylbenzoquinone corresponded to those values identified in the literature [Shin Jikken Kagaku Koza, 15, published by Maruzen 1976)].
Workup
- custom(In some cases, a dimer precipitates in the reaction solution (from 0 to 10%), but it
- customcan readily be removed by filtration
- addition) After adding a small amount of a sodium thiosulfate solution
- extractionthe reaction mixture was extracted with ether
- dry with materialThe ether layer was dried over magnesium sulfate
- distillationsubjected to distillation under reduced pressure
- customto remove the ether
- customThe residue was purified by a silica gel column (
Sources & evidence
- ORD record
- ord-01fa5d1e77a44565a22caa77960edc86
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04482493
Reaction notes
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