Water → HCID 12881466, compound

HRID 637890Notes

Reaction equation

HRID 637890 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][CH2:20][CH2:21][C:22]1[C:27]([OH:28])=[C:26]([O:29][CH3:30])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1[CH3:33].N(S([O-])(=O)=O)(S([O-])(=O)=[O:37])[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][CH2:20][CH2:21][C:22]1[C:27](=[O:28])[C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[C:24](=[O:37])[C:23]=1[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 516951Monobasic potassium phosphateHCID 3032624Potassium nitrosodisulfonateHCID 128326636-(20-Hydroxyeicosyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 12881466HCID 12881466, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(20-hydroxyeicosyl)-2,3-dimethoxy-5-methylphenol (2.3 g) in dimethylformamide (1.5 l) are added potassium nitrosodisulfonate (30 g), water (1.5 l), methanol (300 ml) and monopotassium phosphate (1.3 g) and the mixture is stirred at room temperature for 45 days. The reaction mixture is extracted with dichloromethane and recrystallized from ether. The above procedure gives 6-(20-hydroxyeicosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.3 g) as yellow needles. Melting point: 85° C.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. customrecrystallized from ether

Sources & evidence

ORD record
ord-d5c621b8866b45f8bb0b544224146e44
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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