Dimethylformamide → Idebenone

HRID 637893

Reaction equation

HRID 637893 reaction equation
CN(C)[CH:3]=[O:4].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22]([OH:23])=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1C>O=O>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:3](=[O:4])[C:18]=1[CH3:19]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 128241262-(10-Hydroxydecyl)-5,6-dimethoxy-3-methylphenol

Product 1

HCID 3686Idebenone

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent

Procedure

To a dimethylformamide solution (50 ml) of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (2.53 g) is added bis(salicylidene)ethylenediiminocobalt(II) (salcomine) (0.1 g) and the mixture is stirred in oxygen streams at atmospheric temperature and pressure for 72 hours. The solvent is then distilled off and the product is extracted with ether. The ethereal layer is washed with water and dried over anhydrous sodium sulfate, and the solvent is distilled off. The above procedure yields 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (2.32 g) as orange-yellow needles melting at 52° C.

Workup

  1. distillationThe solvent is then distilled off
  2. extractionthe product is extracted with ether
  3. washThe ethereal layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-89389e2d066544e2a89c18db6e62ed8f
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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