Hydrochloric Acid → (4,5-Dimethylfuran-2-yl)-phenyl-methanone

HRID 228808

Reaktionsgleichung

Reaktionsgleichung von HRID 228808
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]1[O:16][CH:17]=[CH:18][C:19]=1[CH3:20].Cl>C(=S)=S>[CH3:20][C:19]1[CH:18]=[C:17]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[O:16][C:15]=1[CH3:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 343372,3-DimethylfuranHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 23078263(4,5-Dimethylfuran-2-yl)-phenyl-methanoneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel2×

Versuchsvorschrift

Carbon disulfide (35 ml) was added to benzoyl chloride (7.3 g) and anhydrous aluminum chloride (7.0 g) under an argon atmosphere, and a solution of 2,3-dimethylfuran (5.0 g) in carbon disulfide (35 ml) was added dropwise thereto at 10° C. The mixture was then stirred for 30 min while raising the temperature to room temperature. 10% Hydrochloric acid (200 ml) was added to the reaction solution, and the mixture was extracted with dichloromethane. The dichloromethane layer was then washed with water and a 5% aqueous sodium bicarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give (4,5-dimethylfuran-2-yl)-phenyl-methanone (2.5 g, yield 25%).

Aufarbeitung

  1. customat 10° C
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe dichloromethane layer was then washed with water
  4. dry with materiala 5% aqueous sodium bicarbonate solution and was dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e9e2f01c69aa448384a99b23645cba13
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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