4-Cyanobenzaldehyde → 1,3-bis(4-cyanophenyl)prop-2-en-1-one

HRID 1586230Notes

Reaction equation

[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:11]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)(=O)[CH3:12]>>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH:11]=[CH:12][C:7]([C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[O:8])=[CH:15][CH:16]=1)#[N:19]

Participants

Reactant 2

HCID 660424-Cyanobenzaldehyde

HCID 740444'-Cyanoacetophenone

Product 1

HCID 46180931,3-bis(4-cyanophenyl)prop-2-en-1-one

Procedure

Part A. Employing methods similar to Example 1 Part A but using 4-cyano benzaldehyde (1.80 gm, 13.8 mmol) and 4-acetyl benzonitrile (1.0 gm, 6.89 mmol), 4-[3-(4-cyanophenyl)-1-oxo-2-propenyl]benzonitrile was isolated as a pale yellow powder, 0.4 gm (20%) MS 259(M+H)+ 1 H NMR (CDCl3): 7.78(d, 2H), 7.6(t, 1H), 7.5-7.0(m, 7H).

Sources & evidence

ORD record: ord-4fb1b7584e5c455e87c6623b4fa6f153
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942544

Reaction notes

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