Water → 2-(4-Ethylphenylmethyl)malononitrile

HRID 1625850Notes

Reaction equation

HRID 1625850 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)[CH3:2].[C:11](#[N:15])[CH2:12][C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][CH:12]([C:11]#[N:15])[C:13]#[N:14])=[CH:5][CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 122315601-(Bromomethyl)-4-ethylbenzene

Product 1

HCID 821115992-(4-Ethylphenylmethyl)malononitrileYield 35.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixed solution of 4-ethylbenzyl bromide (10.0 g), malononitrile (6.64 g), potassium carbonate (6.94 g) and tetra-n-butylammonium bromide (648 mg) in toluene (100 ml) was agitated at room temperature for 17 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate twice. The extract was washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to give 2-(4-ethylphenylmethyl)malononitrile (3.28 g) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washThe extract was washed successively with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-8569e66c59c14cd2b12c7d3c3316626e
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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