Hydrochloric Acid → Duroquinone

HRID 1979667Notes

Reaction equation

HRID 1979667 reaction equation
Cl.[CH3:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH3:11])[C:4]=1[OH:12].[OH:13]O>CCOCC.O.C(O)(=O)C>[CH3:11][C:5]1[C:4](=[O:12])[C:3]([CH3:2])=[C:8]([CH3:9])[C:7](=[O:13])[C:6]=1[CH3:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 106942,3,5,6-Tetramethylphenol

Product 1

HCID 68238DuroquinoneYield 55%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To 30 mg of the catalyst prepared in the same manner as in Example 19, 100 mg of water was added and stirred, and then 5 ml of an acetic acid solution containing 1% of hydrochloric acid was added. While cooling the mixture with water, 500 mg of 2,3,5,6-tetramethylphenol and 1 g of a 31% hydrogen peroxide aqueous solution were added, and the mixture was stirred for 2.5 hours. After the completion of the reaction, the mixture was diluted with ether, and the catalyst was filtered and washed successively with a NaHCO3 aqueous solution and a saturated sodium chloride aqueous solution. The filtrate was dried over MgSO4 and then concentrated, and the residue was purified by silica gel chromatography by eluting it with a solvent mixture of hexane-dichloromethane (1:1), whereby 300 mg (55% yield) of tetramethylbenzoquinone was obtained.

Workup

  1. additionwas added
  2. additionwas added
  3. additionwere added
  4. stirringthe mixture was stirred for 2.5 hours
  5. customAfter the completion of the reaction
  6. filtrationthe catalyst was filtered
  7. washwashed successively with a NaHCO3 aqueous solution
  8. dry with materialThe filtrate was dried over MgSO4
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel chromatography
  11. washby eluting it
  12. additionwith a solvent mixture of hexane-dichloromethane (1:1)

Sources & evidence

ORD record
ord-55ce7d9155014af9acc037cced3b8af7
Source dataset
uspto-grants-1984_11
Patent number
US04482493

Reaction notes

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