3-Chlorobenzaldehyde → m-Chlorobenzylidene-p-chlorophenylacetonitrile

HRID 1806677Notes

Reaction equation

HRID 1806677 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[OH-].[Na+]>CC(O)C>[Cl:11][C:12]1[CH:13]=[C:14](/[CH:15]=[C:6](/[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)\[C:7]#[N:8])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 912043m-Chlorobenzylidene-p-chlorophenylacetonitrileYield 850.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Method A To a solution of 4-chlorobenzyl cyanide (5.62 g, 4.00 mmol) and 3-chloro-benzaldehyde (Aldrich) (6.06 g, 4.00 mmol) in iPrOH (250 mL) was added 4 N NaOH (5 mL) dropwise at rt and the reaction mixture was stirred at rt for 10 min to give a white suspension. The solid was filtered and washed with water and iPrOH and then dried overnight in vacuum to give (Z)-3-(3-chloro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile (9.33 g, 85.1%) as a white powder which was used in the next step without further purification.

Workup

  1. customto give a white suspension
  2. filtrationThe solid was filtered
  3. washwashed with water and iPrOH
  4. customdried overnight in vacuum

Sources & evidence

ORD record
ord-fa533b3d111442fca83986fd77611a59
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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