Potassium Iodide → 4-(2,4-Dichlorophenoxy)-3-(2-oxopropoxy)-benzonitrile

HRID 646195Notes

Reaction equation

HRID 646195 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[OH:13].Cl[CH2:20][C:21](=[O:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[O:13][CH2:20][C:21](=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 25023955HCID 25023955, compound

Product 1

HCID 686147654-(2,4-Dichlorophenoxy)-3-(2-oxopropoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21.56 g of 4-(2,4-dichlorophenoxy)-3-hydroxybenzonitrile, 14.2 g of chloroacetone, 12.8 g of potassium carbonate and 170 mg of potassium iodide are dissolved in 300 ml of acetone and boiled under reflux for 5 h. After cooling, the precipitate is filtered, concentrated by evaporation, redissolved in ethylacetate and washed with a 1N aqueous solution of sodium hydroxide, water, a 1N aqueous solution of hydrogen chloride and finally with brine. The organic phase is dried over magnesium sulfate and evaporated. The residue is recrystallized from ethylacetate/hexane to yield 4-(2,4-dichlorophenoxy)-3-(2-oxopropoxy)-benzonitrile.

Workup

  1. temperatureunder reflux for 5 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered
  4. concentrationconcentrated by evaporation
  5. dissolutionredissolved in ethylacetate
  6. washwashed with a 1N aqueous solution of sodium hydroxide, water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customevaporated
  9. customThe residue is recrystallized from ethylacetate/hexane

Sources & evidence

ORD record
ord-8ae83f0512bd44e5bf4dc21545d32d88
Source dataset
uspto-grants-2010_04
Patent number
US07705047B2

Reaction notes

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