Oxygen → 6-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 1903425Notes

Reaction equation

HRID 1903425 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][CH2:22][CH2:23][C:24]1[C:29]([OH:30])=[C:28]([O:31][CH3:32])[C:27]([O:33][CH3:34])=[CH:26][C:25]=1[CH3:35].[O:36]=O>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][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[C:29](=[O:30])[C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26](=[O:36])[C:25]=1[CH3:35]

Participants

4

Reactant 2

HCID 977OxygenHCID 128241256-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128241306-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (200 ml) are suspended 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methyl phenol (300 mg) and bis(4-hydroxysalicylidene)ethylenediiminocobalt(II) (50 mg). The suspension is stirred in an oxygen gas stream at ambient temperature and atmospheric pressure for 7 days. The insoluble matter is filtered off and the filtrate is concentrated under reduced pressure. The residue is diluted with water and extracted with ethyl acetate. The extract is treated in a conventional manner and the product is chromatographed on a silica gel column. The fractions obtained by elution with chloroform are pooled and recrystallized from ethanol to give orange-yellow needles of 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I, n=22). m.p. 89°-90.5° C.

Workup

  1. filtrationThe insoluble matter is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionThe residue is diluted with water
  4. extractionextracted with ethyl acetate
  5. additionThe extract is treated in a conventional manner
  6. customthe product is chromatographed on a silica gel column
  7. customThe fractions obtained by elution with chloroform
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e94624aecc964264a3b18c7783d81f63
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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