Acetonitrile → 3-(Trifluoromethyl)benzoylacetonitrile

HRID 2059226

Reaktionsgleichung

Reaktionsgleichung von HRID 2059226
[H-].[Na+].C1COCC1.C(O[C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)C.[C:23](#[N:25])[CH3:24]>CCOCC>[F:21][C:18]([F:19])([F:20])[C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[C:11]([CH2:24][C:23]#[N:25])=[O:22]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 144790Benzoic acid, 3-(trifluoromethyl)-, ethyl ester

Produkt 1

HCID 5203043-(Trifluoromethyl)benzoylacetonitrileAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

NaH (4.8 grams in a 50% oil dispersion) was placed in a 500 ml. 3-necked flask under an atmosphere of nitrogen and, after the addition of 80 ml. of THF, the mixture was heated to reflux. Next a solution of ethyl-3-(trifluoromethyl)benzoate (19 grams), acetonitrile, (5 grams) and THF (20 ml.) was added. Reflux was continued for 2 hours and then the reaction mixture was cooled and 250 ml. ether added. The organic layer was first extracted with 1 N NaOH, and then washed with brine and dried. Removal of the solvent afforded 11 grams of solid product, m.p. 58°-60° C.

Aufarbeitung

  1. addition3-necked flask under an atmosphere of nitrogen and, after the addition of 80 ml
  2. temperatureReflux
  3. temperaturethe reaction mixture was cooled
  4. extractionThe organic layer was first extracted with 1 N NaOH
  5. washwashed with brine
  6. customdried
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3995adbe6b7940e3b474099fd603358c
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04322429

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