Ethyl Acetate → 2-(2,3,5-Trichlorophenyl)-3-oxobutyronitrile

HRID 846356Notes

Reaction equation

HRID 846356 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH2:14][C:15]#[N:16].C(OCC)(=O)C>C(O)C>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH:14]([C:2](=[O:3])[CH3:1])[C:15]#[N:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 197050992-(2,3,5-Trichlorophenyl)acetonitrile

Product 1

HCID 197050532-(2,3,5-Trichlorophenyl)-3-oxobutyronitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOEt (from 0.68 g of sodium) in ethanol (20 ml) was added 2,3,5-trichlorophenylacetonitrile (5 g) and ethyl acetate (4.43 ml). The mixture was heated under reflux, under nitrogen for 2.5 hours. The mixture was left standing at room temperature overnight. The mixture was then concentrated and the residue was dissolved in water. The aqueous phase was washed with ether, acidified with concentrated H2SO4 and extracted with ether. The extracts were bulked, dried (MgSO4) and evaporated, 2.59 g, mp. 134°-135° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux, under nitrogen for 2.5 hours
  3. waitThe mixture was left
  4. concentrationThe mixture was then concentrated
  5. dissolutionthe residue was dissolved in water
  6. washThe aqueous phase was washed with ether
  7. extractionextracted with ether
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-80584a5ab44b4b01b2b6aa19e5e334e4
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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