Methanol → HCID 12832655, compound

HRID 1903434Notes

Reaction equation

HRID 1903434 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.CO>CN(C)C=O>[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

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3032624Potassium nitrosodisulfonateHCID 20254623HCID 20254623, compound

Product 1

HCID 12832655HCID 12832655, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(18-Hydroxyoctadecyl)-2,3-dimethoxy-5-methylphenol (0.5 g), prepared by deacetylating the above 18-acetoxy compound in the same manner as in Reference Example 3, is dissolved in dimethylformamide (1 l) followed by addition of potassium nitrosodisulfonate (13 g), water (700 ml), methanol (100 ml) and potassium-dihydrogen phosfate (1 g). The mixture is stirred at room temperature for 45 days. The product is extracted in a conventional manner and recrystallized from hexane to give yellow needles of 6-(18-hydroxyoctadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I, n=18, 0.31 g). m.p. 81° C.

Workup

  1. extractionThe product is extracted in a conventional manner
  2. customrecrystallized from hexane

Sources & evidence

ORD record
ord-945cdb2094884dbba6a8c2041da947e2
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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