Benzaldehyde → 1-(4-Cyanophenyl)-3-phenyl-2-propen-1-one

HRID 77683

Reaktionsgleichung

Reaktionsgleichung von HRID 77683
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].O.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH:2]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:6]=1)#[N:9]

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 740444'-Cyanoacetophenone

Produkt 1

HCID 542282551-(4-Cyanophenyl)-3-phenyl-2-propen-1-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Acetylbenzonitrile (44al, 1.00 g, 6.9 mmol), sodium hydroxide (0.40 g, 10.0 mmol) and water (20 ml) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. Benzaldehyde (1b, 0.70 ml, 6.9 mmol) was added and the mixture stirred for 2 hr at room temperature. The resulting mixture was filtered and recrystallized from ethanol to give 1.46 g (91%) of a yellow solid: mp 120° C. [expected mp 119-120° C.]; 1H NMR: δ 7.34 (m, 3H), 7.62 (m, 2H), 7.80 (m, 4H), 8.06 (d, 2H, J=8.1 Hz); 13C NMR: δ 115.9, 117.9, 121.1, 128.6, 128.8, 129.0, 131.0, 132.4, 134.3, 141.4, 146.4, 188.9.

Aufarbeitung

  1. stirringthe mixture stirred for 2 hr at room temperature
  2. filtrationThe resulting mixture was filtered
  3. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-20fe1f4c5d734d25862d28e35154e424
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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