Hydrochloric Acid → Idebenone acid

HRID 1248593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248593
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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 10020898Idebenone acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-474df61643f44d509d91a7fc0f28d945
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04525361

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