Ethyl Acetate → (3,5-Dinitrophenoxy)-acetonitrile

HRID 1106735Notes

Reaction equation

HRID 1106735 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].Br[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(=O)CC>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[O:13][CH2:15][C:16]#[N:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 114593,5-DinitrophenolHCID 11534Bromoacetonitrile

Product 1

HCID 18789652(3,5-Dinitrophenoxy)-acetonitrileYield 61.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

3,5-Dinitrophenol (15.0 g) and 10.75 g of bromoacetonitrile were dissolved in 85 ml of 2-butanone and the solution was treated with 33.78 g of potassium carbonate. The heterogenous mixture was stirred and heated at 70° C. for 5 hours, cooled to room temperature, poured into ethyl acetate, washed with water, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography eluting with dichloromethane/hexane (3:1) to give 11.24 g of (3,5-dinitrophenoxy)-acetonitrile as a light yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane/hexane (3:1)

Sources & evidence

ORD record
ord-ce724fe79c6249f485e543f68f804d4f
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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