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3,4,5-Trimethoxytoluene → 6-(11-Acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol

HRID 1903426
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1903426
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH3:34])[CH:27]=[C:28]([O:32]C)[C:29]=1[O:30][CH3:31]>ClCCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:27]1[C:28]([OH:32])=[C:29]([O:30][CH3:31])[C:24]([O:23][CH3:22])=[CH:25][C:26]=1[CH3:34])=[O:16])(=[O:3])[CH3:2]
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Komponenten

5

Edukt 3

HCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 1311378611-Chloro-11-oxoundecyl acetate

Produkt 1

HCID 204311686-(11-Acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenolAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a solution (150 ml) of 11-acetoxy-n-undecanoyl chloride (27.6 g) in 1,2-dichloroethane is added aluminum chloride (28 g), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is cooled to 5° C. followed by addition of a solution (50 ml) of 3,4,5-trimethoxytoluene (19.1 g) in 1,2-dichloroethane and the whole mixture is stirred at room temperature for 72 hours. The reaction mixture is then heated to 50°-60° C. and stirred for 30 minutes. After cooling, 300 ml of ice water is added to the reaction mixture and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and dried over anhydrous magnesium sulfate, and the solvent is distilled off to give a light-yellow oil of 6-(11-acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol (33 g).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to 5° C.
  2. stirringthe whole mixture is stirred at room temperature for 72 hours
  3. temperatureThe reaction mixture is then heated to 50°-60° C.
  4. stirringstirred for 30 minutes
  5. temperatureAfter cooling
  6. extractionthe product is extracted with dichloromethane
  7. washThe dichloromethane layer is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-8ef1e1c66ddf456eb36f569ded189789
Quelldatensatz
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04436753

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