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

HRID 637888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637888
[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].O.CO.P(O)(O)([O-])=[O:33].[K+]>CN(C)C=O>[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:33])[C:18]=1[CH3:28])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 516951Monobasic potassium phosphateHCID 130652366-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methylphenol

Produkt 1

HCID 128814656-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneAusbeute 319,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  1. extractionThe reaction mixture is subjected to extraction with dichloromethane
  2. washthe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent is distilled off
  5. customto thereby leave crude crystals
  6. customThe product is recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-085afd406ac64bc09b5771cbf19dcfee
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559177

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