Acetone → 6-(17-Carboxyheptadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 2412837Notes

Reaction equation

HRID 2412837 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](=[O:26])[C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[C:22](=[O:31])[C:21]=1[CH3:32].CC(C)=[O:35]>S(=O)(=O)(O)O.O>[C: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:31])[C:21]=1[CH3:32])([OH:35])=[O:1]

Participants

5

Reactant 2

HCID 180Acetone2×HCID 12832655HCID 12832655, compound

Product 1

HCID 128240796-(17-Carboxyheptadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

In 10 ml of acetone is dissolved 172 mg of 6-(18-hydroxyoctadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (V:n=17). Separately, 2.672 g of chromic anhydride is dissolved in 2.3 ml of concentrated sulfuric acid and diluted with water to 10 ml. This diluted solution (0.5 ml) is added to the above acetone solution and the mixture is stirred under ice-cooling for 10 minutes. The reaction mixture is diluted with water and extracted with chloroform. The extract is washed with water and dried, and the solvent is distilled off under reduced pressure. The residue is column-chromatographed on silica gel, elution is carried out with chloroform and the eluate is recrystallized from ethanol. The above procedure yields 65 mg of 6-(17-carboxyheptadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I:n=17, R=H) as orange-yellow crystals, m.p. 77°-79° C.

Workup

  1. temperaturecooling for 10 minutes
  2. extractionextracted with chloroform
  3. washThe extract is washed with water
  4. customdried
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is column-chromatographed on silica gel, elution
  7. customthe eluate is recrystallized from ethanol

Sources & evidence

ORD record
ord-a9cd259e5a534682a5795a6f9017438f
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

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