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

HRID 727472

Reaktionsgleichung

Reaktionsgleichung von HRID 727472
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].OO.C(N(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=[O:18].[Na+].[Na+].[Na+].[Na+].[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[CH3:8][C:7]1[C:6](=[O:18])[CH:5]=[C:4]([CH3:9])[C:3](=[O:10])[C:2]=1[CH3:1]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 8779Pentasodium PentetateHCID 170162,3,6-Trimethylphenol

Produkt 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Ausbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of 13.6 g (100 mmol) of 2,3,6-trimethylphenol in 40 ml of acetic acid and 62.3 g (550 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 a pentasodiumdiethylenetriaminepentaacetate 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. 12.6 g (84%) of 2,3,5-trimethyl-p-benzoquinone were obtained in the form of yellow oily crystals.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9784576a2d34442bab21d6e51345079a
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712416

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