Sulfuric Acid → Ethyl 2,4-dioxoheptanoate

HRID 1090156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090156
[O-]CC.[Na+].[CH3:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9].[C:11]([O:18][CH2:19][CH3:20])(=[O:17])[C:12]([O:14]CC)=O.S(=O)(=O)(O)O>C(O)C>[O:14]=[C:12]([CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[C:11]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 78952-PentanoneHCID 2723922Sodium ethoxide

Produkt 1

HCID 3006750Ethyl 2,4-dioxoheptanoateAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To refluxing solution of sodium ethoxide (51.2 g, 0.75 mmol) in ethanol (170 ml) was added dropwise over 30 minutes a solution of 2-pentanone (59 g, 0.68 mol) in diethyl oxalate (99 g, 0.68 mol). The resulting turbid yellow mixture was refluxed further for 2 hours, cooled to room temperature, poured over 500 g ice with stirring and adjusted to pH 1-2 with concentrated sulfuric acid (~40 ml). The organic phase was extracted with benzene (3×300 ml), washed once with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, before being filtered, concentrated, and fractionally distilled at 0.1 mm Hg to give 48.2 g (38%) of the title compound as a yellow liquid; b.p. 85°-95° C.

Aufarbeitung

  1. temperatureThe resulting turbid yellow mixture was refluxed further for 2 hours
  2. extractionThe organic phase was extracted with benzene (3×300 ml)
  3. washwashed once with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationbefore being filtered
  6. concentrationconcentrated
  7. distillationfractionally distilled at 0.1 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-8b163f6127784178b3995fd537c5cfdf
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081127

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