Water → 6-Methyl-2-nitrophenylpyruvic acid

HRID 1953851

Reaktionsgleichung

Reaktionsgleichung von HRID 1953851
[Na].[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH3:12])([O-:4])=[O:3].[C:13](OCC)(=[O:19])[C:14]([O:16]CC)=[O:15].O>C(O)C>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=1[CH2:12][C:13](=[O:19])[C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 7268Diethyl OxalateHCID 5360545Sodium

Produkt 1

HCID 211942326-Methyl-2-nitrophenylpyruvic acidAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium metal (3.80 g, 165 mmol) was dissolved in absolute ethanol (66 mL) at 0° C. The 3-nitro-o-xylene (10 g, 66.2 mmol) and diethyl oxalate (18 mL, 132 mmol) were then added and the reaction was warmed to room temperature and stirred for 18 hours. The reaction was refluxed for 30 minutes, then cooled and water (22 mL) was added and the reaction was stirred at room temperature for one hour. The reaction was concentrated to remove the ethanol, then extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated to provide the desired product (13.92 g, 94%).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 30 minutes
  2. temperaturecooled
  3. stirringthe reaction was stirred at room temperature for one hour
  4. concentrationThe reaction was concentrated
  5. customto remove the ethanol
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-99e359eefa6243b5908a714353b47a5f
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117885

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