Diethyl Ether → 2,4-Dichlorobenzylidenemalononitrile

HRID 983832

Reaction equation

HRID 983832 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].C(OCC)C>C(O)CCC.N1CCCCC1>[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

6

Reactant 3

HCID 3283Diethyl EtherHCID 8010MalononitrileHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 180892,4-Dichlorobenzylidenemalononitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 2631-ButanolSolvent

Procedure

Under an atmosphere of argon, 2,4-dichlorobenzaldehyde (30.00 g, 171 mmol) and malononitrile (13.59 g, 206 mmol) were suspended in 1-butanol (350 ml). After stirring for 15 min, 8 drops of piperidine were added at room temperature. After stirring for an additional 3 h, diethyl ether was added. The precipitate was filtered and washed with diethyl ether and hexane to give the title compound, MS: m/e=222.8 (M+), as a colorless solid (35.34 g, 92%).

Workup

  1. stirringAfter stirring for an additional 3 h
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether and hexane

Sources & evidence

ORD record
ord-5500adcfe11f4975895e20aa0422a449
Source dataset
uspto-grants-2005_03
Patent number
US06867205B2

Linked notes

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