Hydrogen Peroxide → Idebenone acid

HRID 1390570Notes

Reaction equation

HRID 1390570 reaction equation
C[O:2][C:3]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:4]=1[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=O.[OH:27]O.O>C(O)(=O)C>[CH3:23][O:22][C:21]1[C:3](=[O:2])[C:4]([CH2:5][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:18]([CH3:26])[C:19](=[O:27])[C:20]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 128240729-(2',3',4'-Trimethoxy-6'-methylbenzoyl)nonanoic acid

Product 1

HCID 10020898Idebenone acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-(2',3',4'-Trimethoxy-6'-methylbenzoyl)nonanoic acid (formula II-1 wherein R=Y=H3CO, X=H, n=8, in the free form) (0.09 part) was reduced with zinc amalgam (0.2 part) by a procedure similar to that described in Example 10 and oxidized with 30% hydrogen peroxide (10 volume parts) in acetic acid. Following the addition of water, the reaction mixture was extracted with diethyl ether (500 volume parts) and the extract was washed with water and dried. The ether was then removed by distillation. The procedure provided 2,3-dimethoxy-5-methyl-6-(9'-carboxynonyl)-1,4-benzoquinone (formula I-2 wherein R=H3CO, n=8, in the free form).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether (500 volume parts)
  2. washthe extract was washed with water
  3. customdried
  4. customThe ether was then removed by distillation

Sources & evidence

ORD record
ord-e003e173945d422c82fb738c79ec1216
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

Loading…