Potassium Carbonate → 3-(4-Nitrophenyl)pentane-2,4-dione

HRID 450089

Reaktionsgleichung

Reaktionsgleichung von HRID 450089
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].I[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[CH:10][CH:11]=1)([O-:17])=[O:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 31261Acetylacetone

Produkt 1

HCID 35304123-(4-Nitrophenyl)pentane-2,4-dioneAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of pentane-2,4-dione (4.41 g, 40 mmol), 1-iodo-4-nitrobenzene (5 g, 20 mmol) and potassium carbonate (11 g, 80 mmol) were heated in DMSO (15 ml) at 120° C. for 3 hr. The reaction mixture was cooled to room temperature, diluted with water (100 ml), and then extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation gave a residue which was chromatographed over silica gel eluting with ethyl acetate/pet ether (5:95) to give 3-(4-nitrophenyl)-pentane-2,4-dione (2.67 g, 60%) as solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. customdried
  4. customEvaporation
  5. customgave a residue which
  6. customwas chromatographed over silica gel eluting with ethyl acetate/pet ether (5:95)

Quellen und Nachweise

ORD-Eintrag
ord-358a4571793c4c279af155eb1a9e2225
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486962B2

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