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

HRID 727475

Reaction equation

HRID 727475 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[C:5]([CH3:11])[C:3]=1[OH:4].OO.C(N(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].[Na+].[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[CH3:9][C:8]1[C:7](=[O:10])[CH:6]=[C:5]([CH3:11])[C:3](=[O:4])[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 8779Pentasodium PentetateHCID 12785Trimethylhydroquinone

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 15.2 g (100 mmol) of 2,3,6-trimethylhydroquinone in 150 ml of acetic acid and a 28.4 g (250 mmol) of 30% by weight aqueous hydrogen peroxide were simultaneously added dropwise to a stirred solution of 0.68 g (2.0 mmol) of iron 5,14-dihydrodibenzo[b,i][5,9,14,18]tetraaza[14]annulene, 2.52 g (2.0 mmol) of a 40% by weight aqueous solution of pentasodium diethylenetriaminepentaacetate and 0.5 ml of concentrated sulfuric acid in 50 ml of acetic acid at 40° C. with cooling. The reaction mixture was then subjected to steam distillation. The distillate was extracted by shaking with methylene chloride. 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 concentrated to a yellow oil, which slowly solidifed. 12.9 g (86%) of 2,3,5-trimethyl-p-benzoquinone were obtained in the form of yellow oily crystals.

Workup

  1. temperaturewith cooling
  2. distillationThe reaction mixture was then subjected to steam distillation
  3. extractionThe distillate was extracted
  4. stirringThe organic phase was shaken with aqueous sodium bicarbonate solution
  5. customwith water, separated from the aqueous phase
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a yellow oil, which

Sources & evidence

ORD record
ord-b7efb740e3224f4294f6cbf4746000b7
Source dataset
uspto-grants-1998_01
Patent number
US05712416

Linked notes

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