Hydrogen Peroxide → 2,3-Dimethyl-2,5-cyclohexadiene-1,4-dione

HRID 727478

Reaction equation

HRID 727478 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[CH:5][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]=[CH:5][C:3](=[O:4])[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 8779Pentasodium PentetateHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 106882,3-Dimethyl-2,5-cyclohexadiene-1,4-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 13.8 g (100 mmol) of 2,3-dimethylhydroquinone in 500 ml of acetic acid and 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 mi of concentrated sulfuric acid in 50 ml of acetic acid at 40° C. with cooling. The mixture was then stirred for 15 min and subsequently subjected to a steam distillation. The distillate was extracted three times with a total of 400 ml of 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 evaporated to dryness to yield 11.8 g (87%) of 2,3-dimethylbenzoquinone in the form of a yellow powder. Melting point 57°-59° C.

Workup

  1. temperaturewith cooling
  2. distillationsubsequently subjected to a steam distillation
  3. extractionThe distillate was extracted three times with a total of 400 ml of methylene chloride
  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. customevaporated to dryness

Sources & evidence

ORD record
ord-efc6b5c6b92443d493aaddb9ac1112c2
Source dataset
uspto-grants-1998_01
Patent number
US05712416

Linked notes

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