Hydrochloric Acid → Idebenone acid

HRID 1679849Notes

Reaction equation

HRID 1679849 reaction equation
N(S([O-])(=O)=O)(S([O-])(=O)=[O:4])[O].[K+].[K+].[OH:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].Cl>O.[OH-].[Na+].CC(C)=O>[CH3:21][O:20][C:19]1[C:14](=[O:13])[C:15]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:16]([CH3:24])[C:17](=[O:4])[C:18]=1[O:22][CH3:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3032624Potassium nitrosodisulfonateHCID 1290613810-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid

Product 1

HCID 10020898Idebenone acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of potassium nitrosodisulfonate (0.8 part) in water (10 volume parts) was added to a solution of 10-(2'-hydroxy-3', 4'-dimethoxy-6'-methylphenyl)decanoic acid (formula II-2 wherein R=H3CO, X=H, Y=OH, n=8, in the free form) (0.097 part) in a mixture of 1% sodium hydroxide (0.67 volume part) and acetone (2 volume parts) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was rendered acidic with dilute hydrochloric acid and extracted with diethyl ether. The extract was washed with water and dried, followed by evaporation to dryness. 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) (0.099 part) as orange-colored needles melting at 59°-60.5° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. customdried
  4. customfollowed by evaporation to dryness

Sources & evidence

ORD record
ord-f5f6da76c18e42a597d993e612412e25
Source dataset
uspto-grants-1981_06
Patent number
US04271083

Reaction notes

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