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

HRID 727474

Reaktionsgleichung

Reaktionsgleichung von HRID 727474
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].S([O-])(O[O-])(=O)=[O:12].[K+].[K+].S(=O)(=O)(O)O>C(O)(=O)C.O>[CH3:8][C:7]1[C:6](=[O:12])[CH:5]=[C:4]([CH3:9])[C:3](=[O:10])[C:2]=1[CH3:1]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 170162,3,6-TrimethylphenolHCID 10313463Potassium peroxymonosulphate

Produkt 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 13.6 g (100 mmol) of 2,3,6-trimethylphenol in 40 ml of acetic acid and a solution of 73.7 g (240 mmol) of 50% by weight potassium peroxomonosulfate in 320 ml of water 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 room temperature 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. 11.1 g (74%) 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-9da68dad0b324541961fdd825f05dd61
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712416

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