Sodium Chloride → 4-(Trifluoromethoxy)benzalmalononitrile

HRID 749600Notes

Reaction equation

HRID 749600 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:14](#[N:18])[CH2:15][C:16]#[N:17].[Cl-].[Na+]>C(O)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:15]([C:14]#[N:18])[C:16]#[N:17])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 8010MalononitrileHCID 69573p-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 8456624-(Trifluoromethoxy)benzalmalononitrileYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 66854Benzyltrimethylammonium hydroxideSolvent

Procedure

First, 10.0 g of 4-(trifluoromethoxy)benzaldehyde and 3.50 g of malononitrile were dissolved in 60 ml of 70% (w/w) aqueous ethanol, to which a catalytic amount of benzyltrimethylammonium hydroxide was added, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from t-butyl methyl ether and hexane to give 9.24 g of (4-(trifluoromethoxy)benzylidene)malononitrile.

Workup

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from t-butyl methyl ether and hexane

Sources & evidence

ORD record
ord-af12c610153149f5929a5a53ac6d02e7
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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