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

HRID 2412840Notes

Reaction equation

HRID 2412840 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 N,N-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 product is extracted with dichloromethane and the dichloromethane layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is then distilled off and the resultant crude crystals are recrystallized from hexane. The above procedure yields 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (6.4 g) as orange-yellow needles, m.p. 41° C.

Workup

  1. extractionThe product is extracted with dichloromethane
  2. washthe dichloromethane layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is then distilled off
  5. customthe resultant crude crystals are recrystallized from hexane

Sources & evidence

ORD record
ord-77e5ac921060463a8916d214e55bb901
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

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