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Ethylene → 3,3'-(1,2-Ethenediyldi-4,1-phenylene)bis-(2-propenenitrile)

HRID 484649
Notes
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Reaction equation

HRID 484649 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)=O.[CH2:14]([N:21](C)C)[C:15]1C=CC=CC=1.C=C.[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:10]([CH:9]=[CH:8][C:7]1[CH:12]=[CH:13][C:4]([CH:2]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:15][C:14]#[N:21])=[CH:29][CH:28]=2)=[CH:5][CH:6]=1)#[N:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6325EthyleneHCID 7681N,N-DimethylbenzylamineHCID 7809P-Xylene2×HCID 53717999HCID 53717999, compound

Product 1

HCID 539295483,3'-(1,2-Ethenediyldi-4,1-phenylene)bis-(2-propenenitrile)Yield 15%

Reagents, catalysts & solvents 1

HCID 167845
palladium(II) acetate
Catalyst

Conditions

Temperature
130 °C

Procedure

3.83 g (20 mmols) of 4-chloroformylcinnamonitrile, 2.70 g (20 mmols) of N-benzyldimethylamine and 0.0448 g (0.2 mmol) of palladium acetate are added under argon to 40 ml of p-xylene. Ethylene is passed through the mixture, which is stirred for 23 hours at 130° C. The reaction mixture is then diluted at 130° C. with 40 ml of p-xylene and is filtered. 10 ml of n-hexane are added to the filtrate. Cooling to room temperature gives 0.39 g (15% of theory) of 4,4'-bis-(2-cyanovinyl)-stilbene, melting point 220° C.

Workup

  1. filtrationis filtered
  2. addition10 ml of n-hexane are added to the filtrate
  3. temperatureCooling to room temperature

Sources & evidence

ORD record
ord-90943814f3c04b36b2c9128607ece27f
Source dataset
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04533505

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes