Oxygen → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-
Reaction equation
O=O.[CH3:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12].S(=O)(=O)(O)[OH:14]>C(O)(=O)C>[CH3:10][C:9]1[C:8](=[O:14])[CH:7]=[C:6]([CH3:11])[C:5](=[O:12])[C:4]=1[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Oxygen was passed into a solution of 0.68 g (2 mmol) of iron 5,14-dihydrodibenzo[b,i][5,9,14,18]tetraaza[14]annulene in 150 ml of 85% by weight aqueous acetic acid and, during this, a solution of 13.6 g (100 mmol) of 2,3,6-trimethylphenol and 0.5 g of concentrated sulfuric acid in 75 ml of 85% by weight acetic acid was added dropwise while stirring vigorously at 40° C. After oxygen uptake ceased, the mixture was subjected to a steam distillation. The distillate was extracted with tert-butyl methyl ether. The organic phase was shaken with aqueous sodium bicarbonate solution and then with water, separated from the aqueous phase, dried over magnesium sulfate, filtered and evaporated to dryness to yield 12.0 g (80%) of 2,3,5-trimethylbenzoquinone in the form of yellow oily crystals.
Workup
- distillationthe mixture was subjected to a steam distillation
- extractionThe distillate was extracted with tert-butyl methyl ether
- stirringThe organic phase was shaken with aqueous sodium bicarbonate solution
- customwith water, separated from the aqueous phase
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1a8b2ecf24064ec198479207b9bb87af
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712416
Reaction notes
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