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

HRID 637891Notes

Reaction equation

HRID 637891 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 128326536-(11-Acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methylphenol (8 g) in dimethylformamide (400 ml) are added potassium nitrosodisulfonate (24 g), water (400 ml), methanol (30 ml) and monopotassium phosphate (1.0 g). The mixture is stirred at room temperature for 28 days. The reaction product is extracted with dichloromethane and the dichloromethane layer is washed with water and dried over magnesium sulfate. The solvent is distilled off to thereby leave crude crystals. The crude crystals are recrystallized from hexane to yield 6.4 g of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as orange-yellow needles, m.p.: 41° C.

Workup

  1. extractionThe reaction product is extracted with dichloromethane
  2. washthe dichloromethane 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 crude crystals are recrystallized from hexane

Sources & evidence

ORD record
ord-533294f5e54a4a9d98778a707d87cf80
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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