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>[CH3:9][C:4]1[C:3](=[O:10])[C:2]([CH3:1])=[C:7]([CH3:8])[C:6](=[O:11])[CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
600 mg of the catalyst prepared in Example 6 and 10 g of 2,3,6-trimethylphenol were added to 90 ml of acetic acid. While cooling the solution with ice water, 20 g of a 30% hydrogen peroxide aqueous solution was dropwise added in about 40 minutes, and the mixture was stirred overnight. After completion of the reaction, the catalyst was removed by filtration, and the acetic acid solution was concentrated under reduced pressure to about 20 ml, diluted with ether, washed with an aqueous solution of NaHCO3 and then dried. The ether was distilled off, and the residue was subjected to distillation under reduced pressure, whereby 8.7 g of trimethylbenzoquinone (boiling point: 64° C./0.7 torr) was obtained. Further, the distillation residue was treated by column chromatography (SiO2 /CH2Cl2), whereby 0.5 g of trimethylbenzoquinone was additionally obtained. The total amount was 9.2 g (84% yield).
Workup
- additionwas dropwise added in about 40 minutes
- customAfter completion of the reaction
- customthe catalyst was removed by filtration
- concentrationthe acetic acid solution was concentrated under reduced pressure to about 20 ml
- additiondiluted with ether
- washwashed with an aqueous solution of NaHCO3
- customdried
- distillationThe ether was distilled off
- distillationthe residue was subjected to distillation under reduced pressure
Sources & evidence
- ORD record
- ord-001e681fde9b4de5a1299e4bc074c077
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04482493
Reaction notes
Loading…