Malononitrile → 2,4-Dichlorobenzylidenemalononitrile

HRID 1094045Notes

Reaction equation

HRID 1094045 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11](#[N:15])[CH2:12][C:13]#[N:14].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:12]([C:11]#[N:15])[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 134042,4-DichlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 180892,4-DichlorobenzylidenemalononitrileYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichlorobenzaldehyde (1.75 g, 10 mmol) and malononitrile (660 mg, 10 mmol) in ethanol (10 ml) was added 200 μL of 10% aqueous KOH. The mixture was stirred at room temperature for 15 min, allowed to stand for 30 min, cooled with ice-bath and then filtered to give 2-(2,4-dichloro-benzylidene)-malononitrile (1a) as a white solid (1.8 g).

Workup

  1. waitto stand for 30 min
  2. temperaturecooled with ice-bath
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8cd2cb4d84c24c72b93e680037822fc8
Source dataset
uspto-grants-2012_03
Patent number
US08133898B2

Reaction notes

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