Sulfuric Acid → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

HRID 727476Notes

Reaction equation

HRID 727476 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1[OH:4].C(OO)(C)(C)C.S(=O)(=O)(O)O>C(O)(=O)C>[CH3:1][C:2]1[C:3](=[O:4])[CH:5]=[C:6]([CH3:11])[C:7](=[O:10])[C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6410tert-Butyl hydroperoxideHCID 12785Trimethylhydroquinone

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 15.2 g (100 mmol) of 2,3,5-trimethylhydroquinone in 150 ml of acetic acid and 16.1 g (125 mmol) of 70% by weight aqueous tert-butyl hydroperoxide 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 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. 11.7 g (78%) 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-0619830e51fe48f4a0e5af5f1e14afd7
Source dataset
uspto-grants-1998_01
Patent number
US05712416

Reaction notes

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