Hydrochloric Acid → 2,9-Diacetylcarbazole

HRID 915259

Reaktionsgleichung

Reaktionsgleichung von HRID 915259
[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[CH3:2].[C:17](Cl)(=[O:19])[CH3:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:17]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:4]([C:1](=[O:3])[CH3:2])[C:5]=2[CH:6]=1)(=[O:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 958379-Acetyl-9H-carbazoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2748702,9-DiacetylcarbazoleAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

9-Acetyl-carbazole (41.85 g, 0.2 mol) was dissolved in 1 L methylene chloride and 28.5 mL acetylchloride (0.4 mol) and 120 g aluminum chloride (0.9 mol) were added and the solution refluxed for 1.5 h. The solution was cooled to −78° C. and 6N HCl was added slowly while stirring and allowed to warm to room temperature. Methylene chloride was added to dissolve the precipitate and the solution was extracted, and the organics dried over Na2SO4, decolorized with charcoal, filtered and concentrated. Recrystallization from benzene/hexane gave 27.9 g 2,9-diacetylcarbazole.

Aufarbeitung

  1. temperaturethe solution refluxed for 1.5 h
  2. temperatureto warm to room temperature
  3. dissolutionto dissolve the precipitate
  4. extractionthe solution was extracted
  5. dry with materialthe organics dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallization from benzene/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4872738299b94557acea9dcfb1b115b9
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265146B2

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