Dimethylformamide → Idebenone

HRID 637894

Reaction equation

HRID 637894 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 (100 ml) of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (4.1 g) is added bis(3-methoxysalicylidene)ethylenediiminocobalt(II) (0.2 g) and the mixture is stirred in oxygen streams at atmospheric temperature and pressure for 72 hours. After the reaction has been completed, the solvent is distilled off and the residue is extracted with ether. The ethereal layer is washed with water and dried, and the solvent is distilled off in the conventional manner. The crude crystals thus obtained are recrystallized from ethyl acetate-hexane (1:3). The above procedure yields 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.77 g) as orange-yellow needles melting at 52° C.-53° C.

Workup

  1. distillationthe solvent is distilled off
  2. extractionthe residue is extracted with ether
  3. washThe ethereal layer is washed with water
  4. customdried
  5. distillationthe solvent is distilled off in the conventional manner
  6. customThe crude crystals thus obtained
  7. customare recrystallized from ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-c74e2c1dabb34e8eaa8b99a4b3f84ac1
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

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