Ethyl Acetate → (4-Methyl-3-nitrophenoxy) acetonitrile

HRID 1106714Notes

Reaction equation

HRID 1106714 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Br[CH2:13][C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(=O)CC>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][C:14]#[N:15])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 162713-Nitro-p-cresol

Product 1

HCID 18789631(4-Methyl-3-nitrophenoxy) acetonitrileYield 97.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

4-Methyl-3-nitrophenol (5.0 g) (TCl America, Portland, Oreg.) and 4.70 g of bromoacetonitrile were dissolved in 30 ml of 2-butanone; then 13.5 g of potassium carbonate was added and the mixture was stirred and heated at 70° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into ethyl acetate, washed with water, dried, and evaporated to give 6.1 g of (4-methyl-3-nitrophenoxy)-acetonitrile as a brown oil. ##STR74##

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-3d250ed0542c4cdd927e425c54264b54
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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