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

HRID 618228Notes

Reaction equation

HRID 618228 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-fe5a47111e5546f59eaaf06879b7ea2b
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

Loading…