Water → 6-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 1903431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903431
[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][CH2:16][C:17]1[C:22]([OH:23])=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH3:28])(=[O:3])[CH3:2].N(S([O-])(=O)=O)(S([O-])(=O)=[O:32])[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][CH2:16][C:17]1[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19](=[O:32])[C:18]=1[CH3:28])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 516951Monobasic potassium phosphateHCID 3032624Potassium nitrosodisulfonateHCID 130652366-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methylphenol

Produkt 1

HCID 128814656-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution (300 ml) of 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methylphenol (6.1 g) in dimethylformamide are added potassium nitrosodisulfonate (18 g), water (300 ml), methanol (50 ml) and potassium dihydrogen phosphate (0.5 g), and the mixture is stirred at room temperature for 30 days. The product is extracted with dichloromethane, and the organic layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off to give crude crystals. This product is recrystallized from hexane to give orange-yellow needles of 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (4.8 g). m.p. 47° C.

Aufarbeitung

  1. extractionThe product is extracted with dichloromethane
  2. washthe organic layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled off
  5. customto give crude crystals
  6. customThis product is recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-a5569572ad524e3e943bfd9d4830af3e
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436753

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