Dimethylformamide → Idebenone

HRID 637896

Reaction equation

HRID 637896 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>N1C=CC=CC=1>[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 1049PyridineSolvent

Procedure

To a dimethylformamide solution (30 ml) of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (1.6 g) are added bis(3-methoxysalicylidene)ethylenediiminocobalt(II) (0.06 g) and pyridine (10 mg), and the mixture is stirred in air streams at atmospheric temperature and pressure for 72 hours. After the reaction has been completed, the reaction product is isolated in the same manner as described in Example 7. The crude crystals thus obtained are recrystallized from ether-hexane (1:3). The above procedure yields 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.1 g) as orange-yellow needles melting at 51° C.-53° C.

Workup

  1. customthe reaction product is isolated in the same manner
  2. customThe crude crystals thus obtained
  3. customare recrystallized from ether-hexane (1:3)

Sources & evidence

ORD record
ord-b1379a744dad4c438cebfe3f8016b01d
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Linked notes

Loading…