Dimethylformamide → Idebenone

HRID 637893

Reaktionsgleichung

Reaktionsgleichung von HRID 637893
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 3686Idebenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 977OxygenLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-89389e2d066544e2a89c18db6e62ed8f
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559177

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