Diethyl 2-(2-(4-nitrophenyl)acetyl)malonate → 1-(4-Nitrophenyl)propan-2-one

HRID 450078

Reaktionsgleichung

Reaktionsgleichung von HRID 450078
C(OC(=O)[CH:5]([C:11](=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)C(OCC)=O)C>CS(C)=O.O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11](=[O:22])[CH3:5])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Komponenten

4

Edukt 1

HCID 12342271Diethyl 2-(2-(4-nitrophenyl)acetyl)malonate

Produkt 1

HCID 2193671-(4-Nitrophenyl)propan-2-oneAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-[2-(4-Nitro-phenyl)-acetyl]-malonic acid diethyl ester (1.4 g) was taken up in a mixture of DMSO (8 ml) and water (4 ml) and heated at 150° C. with stirring for 10 hr. The product was extracted with ethyl acetate (50 ml). The organic layer was washed with water, aqueous sodium bicarbonate solution and brine. The organic layer was then dried over sodium sulphate, filtered and evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (6:94) as eluent yielded 1-(4-nitro-phenyl)-propan-2-one (160 mg, 24%).

Aufarbeitung

  1. extractionThe product was extracted with ethyl acetate (50 ml)
  2. washThe organic layer was washed with water, aqueous sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c2c54cfd496341b4a512b49e11d95194
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486962B2

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