Water → 6-(11-Acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 1903429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903429
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21]([OH:22])=[C:20]([O:23][CH3:24])[C:19]([O:25][CH3:26])=[CH:18][C:17]=1[CH3:27])(=[O:3])[CH3:2].N(S([O-])(=O)=O)(S([O-])(=O)=[O:31])[O].[K+].[K+].O.P([O-])(O)(O)=O.[K+]>CN(C)C=O.CO>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:31])[C:17]=1[CH3:27])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 516951Monobasic potassium phosphateHCID 3032624Potassium nitrosodisulfonateHCID 20254624HCID 20254624, Verbindung

Produkt 1

HCID 128326536-(11-Acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution (400 ml) of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methylphenol (8 g) in dimethylformamide are added potassium nitrosodisulfonate (24 g), water (400 ml), methanol (30 ml) and potassium dihydrogen phosphate (1.0 g), and the mixture is stirred at room temperature for 28 days. The product is extracted with dichloromethane and the dichloromethane layer is washed with water and then dried over anhydrous magnesium sulfate. Removal of the solvent by distillation gives crude crystals. Recrystallization from hexane yields orange-yellow needles of 6.4 g of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone. m.p. 41° C.

Aufarbeitung

  1. extractionThe product is extracted with dichloromethane
  2. washthe dichloromethane layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent
  5. distillationby distillation
  6. customgives crude crystals
  7. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-370c4f83c4524ae090c5c4a2fe360aae
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436753

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