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Ethanol → Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-

HRID 1589093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1589093
[Na].C(O)C.[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.[C:18]1([CH2:24][C:25](OCC)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:5][C:6]([F:16])([F:17])[C:7]1[CH:8]=[C:9]([CH:13]([C:25]([CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 7590Ethyl phenylacetateHCID 75360m-TrifluoromethylphenylacetonitrileHCID 5360545Sodium2×

Produkt 1

HCID 106559Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-Ausbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

In this example, 4.91 g of metallic sodium was added to 110 ml of anhydrous ethanol at room temperature and stirred until all of the sodium dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl)acetonitrile and 21.73 g of ethyl phenylacetate was then added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml water and extracted three times with ethyl ether. The pH of the extracted aqueous layer was adjusted to a pH of about 1 with aqueous 10 wt. % hydrochloric acid and again extracted three times with ethyl ether. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under vacuum affording 22.6 g of the title compound.

Aufarbeitung

  1. dissolutiondissolved
  2. additionwas then added dropwise
  3. temperatureat reflux for about 18 hours
  4. extractionextracted three times with ethyl ether
  5. extractionagain extracted three times with ethyl ether
  6. washThe organic layer was washed twice with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-49605d1b4eb54723b0e3d3e2e958f459
Quelldatensatz
uspto-grants-1986_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04568376

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