Acrylonitrile → 4-(3-Chlorophenyl)-4-oxobutanenitrile

HRID 1763593Notes

Reaction equation

HRID 1763593 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8](N2CCOCC2)[C:9]#N)[CH:5]=[CH:6][CH:7]=1.[O:17]1CCCC1.[OH-].[K+].[C:24](#[N:27])[CH:25]=C>CO.O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([CH2:9][CH2:25][C:24]#[N:27])=[O:17]

Participants

8

Reactant 4

HCID 7855AcrylonitrileHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 11241857HCID 11241857, compound

Product 1

HCID 125694054-(3-Chlorophenyl)-4-oxobutanenitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 23.6 g. of α-(m-chlorophenyl)-4-morpholineacetonitrile in 100 ml. of tetrahydrofuran is added 120 drops of a 30% solution of KOH in methanol. To the mixture is added 4.1 ml. of acrylonitrile (temperature rose to 45° C.). After stirring 1 hr., the mixture is concentrated to dryness under vacuum. The residue is dissolved in methylene chloride and passed through a short column of hydrous magnesium silicate. The eluent is concentrated under vacuum to give 36.6 g. of a yellow oil. The oil is heated (steam bath) with a mixture of 150 ml. of acetic acid and 10 ml. of water for 1 hr. The solvent is removed under vacuum and the residue treated with water. The mixture is filtered to give 18.8 g. of crystals, m.p. 49°-51° C.

Workup

  1. additionTo the mixture is added 4.1 ml
  2. concentration, the mixture is concentrated to dryness under vacuum
  3. dissolutionThe residue is dissolved in methylene chloride
  4. concentrationThe eluent is concentrated under vacuum
  5. customto give 36.6 g
  6. temperatureThe oil is heated (steam bath)
  7. additionwith a mixture of 150 ml
  8. customThe solvent is removed under vacuum
  9. additionthe residue treated with water
  10. filtrationThe mixture is filtered
  11. customto give 18.8 g

Sources & evidence

ORD record
ord-58bbe1e9e5eb4569a3aa46d7341354b3
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

Loading…