Pyridine → 2-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

HRID 864694

Reaktionsgleichung

Reaktionsgleichung von HRID 864694
[CH3:1][O:2][C:3]1[C:4](=[O:24])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:5]1[C:4](=[O:24])[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[C:7](=[O:11])[C:6]=1[CH3:12])(=[O:33])[CH3:32]

Komponenten

5

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. temperaturecooling
  2. stirringAfter stirring for 1 hour at the same temperature
  3. washthe mixture was washed with 0.1N hydrochloric acid (50 ml)
  4. concentrationThe dichloromethane layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c8f3ba3b591c47dab4889d4ffc3b83e3
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563129

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