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

HRID 77683

Reaction equation

HRID 77683 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-20fe1f4c5d734d25862d28e35154e424
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Linked notes

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