Acetic Acid → 4-(2-Acetyl-3-oxo-1-butenyl)benzonitrile

HRID 1951377

Reaktionsgleichung

Reaktionsgleichung von HRID 1951377
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[CH3:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15].C(O)(=O)C.N1CCCCC1>ClCCl>[C:14]([C:13]([C:12](=[O:17])[CH3:11])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)(=[O:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 660424-Cyanobenzaldehyde

Produkt 1

HCID 3674534-(2-Acetyl-3-oxo-1-butenyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.3 g (17.5 mmol) of 4-formylbenzonitrile, 1.98 ml (19.29 mmol) of 2,4-pentanedione, 1 ml (26 mmol) of acetic acid and 0.34 ml (3.5 mmol) of piperidine in 40 ml of anhydrous dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from diethyl ether. 3.18 g (85% of theory) of the title compound are obtained as a pale brown solid.

Aufarbeitung

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4bdd19e40c9348fd815fbb2abf86bdab
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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