Water → HCID 12832655, compound

HRID 637910Notes

Reaction equation

HRID 637910 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[C:25]([OH:26])=[C:24]([O:27][CH3:28])[C:23]([O:29][CH3:30])=[CH:22][C:21]=1[CH3:31].N(S([O-])(=O)=O)(S([O-])(=O)=[O:35])[O].[K+].[K+].O.P(O)(O)([O-])=O.[K+]>CN(C)C=O.CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[C:25](=[O:26])[C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[C:22](=[O:35])[C:21]=1[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 516951Monobasic potassium phosphateHCID 3032624Potassium nitrosodisulfonateHCID 20254623HCID 20254623, compound

Product 1

HCID 12832655HCID 12832655, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The above 18-acetoxy compound was deacetylated by the corresponding procedure of Example 6 and the resultant 6-(18-hydroxyoctadecyl)-2,3-dimethoxy-5-methylphenol (0.5 g) is dissolved in dimethylformamide (1 l). To this solution is added potassium nitrosodisulfonate (13 g), 700 ml of water, 100 ml of methanol and monopotassium phosphate (1 g), and the mixture is stirred at room temperature for 45 days. The product is extracted in the conventional manner and recrystallized from ether-hexane. The above procedure yields 6-(18-hydroxyoctadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as yellow needles (0.31 g), m.p. 81° C.

Workup

  1. extractionThe product is extracted in the conventional manner
  2. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-cfb28e57c75d4693b9ecf279b3209f33
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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