Sodium Dithionite → 6-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone

HRID 864695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864695
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[C:28](=[O:29])[C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[C:25](=[O:34])[C:24]=1[CH3:35])(=[O:11])[CH3:10]>CCOCC.O>[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[C:28]([OH:29])=[C:27]([O:30][CH3:31])[C:26]([O:32][CH3:33])=[C:25]([OH:34])[C:24]=1[CH3:35])(=[O:11])[CH3:10]

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 110902052-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

Produkt 1

HCID 152949936-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2,3-Dimethoxy-6-(10-hydroxydecyl)-5-methyl-1,4-benzoquinone (3.38 g) was dissolved in dichloromethane (50 ml). Pyridine (1 ml) was added, and acetyl chloride (0.8 ml) was added with stirring under ice-cooling. After stirring for 1 hour at the same temperature, the mixture was washed with 0.1N hydrochloric acid (50 ml) followed by water (50 ml). The dichloromethane layer was concentrated under reduced pressure to obtain 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-l,4-benzoquinone as a red oil. This oil was dissolved in ether (50 ml), and a solution of sodium hydrosulfite (4 g) in water (50 ml) was added. Stirring was continued at room temperature until the red color of the ether layer disappeared. The ether layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the desired compound (3.8 g) as a pale yellow oil.

Aufarbeitung

  1. customThe ether layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09cbc00dde7647faa01f2fc901bc85ee
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563129

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