Idebenone → 10-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-YL)decanal

HRID 2166245Notes

Reaction equation

HRID 2166245 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[OH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33](=[O:34])[C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[C:30](=[O:39])[C:29]=1[CH3:40]>ClCCl>[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33](=[O:34])[C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[C:30](=[O:39])[C:29]=1[CH3:40])=[O:17]

Participants

5

Reactant 3

HCID 3686IdebenoneHCID 517045Sodium Acetate2×HCID 178418287HCID 178418287, compound2×

Product 1

HCID 1351855510-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-YL)decanalYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (3.3 g) and sodium acetate (0.5 g) were suspended in dichloromethane (2.5 ml). To the suspension was added a solution of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.38 g) in dichloromethane (20 ml) at room temperature. The mixture was stirred for an hour. Then, additional amount of pyridinium chlorochromate (1 g) and sodium acetate (0.5 g) were added and the mixture was stirred for another 1.5 hours. The reaction mixture was poured into an ice water and the mixture was extracted with ethyl acetate. The extract was treated in a conventional manner and the residue obtained was purified by column chromatography using silica gel. Elution was carried out with dichloroethane-ethyl acetate (9:1) and then with carbon tetrachloride-ethyl acetate (9:1), and the eluate was recrystallized from ethyl acetate-hexane to give 6-(9-formylnonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.3 g), melting at 44.5°-46.5° C.

Workup

  1. stirringthe mixture was stirred for another 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. additionThe extract was treated in a conventional manner
  4. customthe residue obtained
  5. customwas purified by column chromatography
  6. washElution
  7. customwith carbon tetrachloride-ethyl acetate (9:1), and the eluate was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-21d6ee4c22b742b482563c5c1b1bf0c6
Source dataset
uspto-grants-1990_07
Patent number
US04943645

Reaction notes

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