Dimethylformamide → 6-(6-Hydroxyhexyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 637898

Reaction equation

HRID 637898 reaction equation
CN(C)[CH:3]=[O:4].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:18]([OH:19])=[C:17]([O:20][CH3:21])[C:16]([O:22][CH3:23])=[CH:15][C:14]=1C>O=O.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:18](=[O:19])[C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[C:3](=[O:4])[C:14]=1[CH3:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 202546196-(6-Hydroxyhexyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 128814636-(6-Hydroxyhexyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (20 ml) of 6-(6-hydroxyhexyl)-2,3-dimethoxy-5-methylphenol (1.5 g) is added bis(salicylidene)ethylenediiminocobalt(II) (15 mg), and the mixture is stirred in oxygen streams at atmospheric temperature and pressure for 72 hours. The reaction product is isolated as in Example 7 and purified by silica gel column chromatography. The ether-hexane (1:1) eluate yields 6-(6-hydroxyhexyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.1 g) as orange-yellow oil.

Workup

  1. customThe reaction product is isolated as in Example 7
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-462b9c8a36eb47669301e031c10faa9d
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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