Dibenzofuran → 2-Acetyldibenzofuran

HRID 1781174

Reaktionsgleichung

Reaktionsgleichung von HRID 1781174
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:18](Cl)(=[O:20])[CH3:19]>ClC(Cl)C>[C:18]([C:6]1[CH:7]=[CH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[C:13]=2[CH:5]=1)(=[O:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 568DibenzofuranHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2930282-AcetyldibenzofuranAusbeute 28,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (23.8 g, 178.4 mmol) was added portionwise to a solution of dibenzofuran (30.0 g, 178.4 mmol) and acetyl chloride (14.0 g, 178.4 mmol) in dichloroethane at 0° C. After 8 hours, the reaction was quenched with 6N HCl. The layers were separated and the methylene chloride layer was dried (MgSO4), filtered and concentrated to provide a yellow solid. The solid was recrystallized 3 times from hexane to provide 10.6 g (28%) of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ 2.7 (s, 3H), 7.4 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.5 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.65 (d, J=7.5 Hz, 2H), 8.0 (d, J=7.5 Hz, 1H), 8.15 (dd, J=7.5 Hz, 0.5 Hz), 8.6 (d, J=0.5 Hz). MS (DCl/NH3) m/e 211 (M+H)+.

Aufarbeitung

  1. customthe reaction was quenched with 6N HCl
  2. customThe layers were separated
  3. dry with materialthe methylene chloride layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a yellow solid
  7. customThe solid was recrystallized 3 times from hexane

Quellen und Nachweise

ORD-Eintrag
ord-b2b29368f8524ef8a54a46dbbda5d4cb
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631401

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