Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile

HRID 1951375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951375
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[CH3:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17].C(O)(=O)C.N1CCCCC1>ClCCl>[C:16]([C:15]([C:14](=[O:19])[CH3:13])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 166592514-Formyl-3-methoxybenzonitrile

Produkt 1

HCID 591869164-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

21 g (130 mmol) of 4-formyl-3-methoxybenzonitrile, 14.7 ml (143 mmol) of 2,4-pentanedione, 11.2 ml (195 mmol) of acetic acid and 2.6 ml (26 mmol) of piperidine in 400 ml of dry 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. 23.2 g (92% 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-7902c796ca9e4929bc8233ebfb11da6c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

Notizen zur Reaktion

Wird geladen…