Furfural → (2Z)-2-(4-chlorophenyl)-3-(2-furyl)-2-propenenitrile

HRID 2255394Notes

Reaction equation

HRID 2255394 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[CH:16][C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 14798Sodium HydroxideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 324048(2Z)-2-(4-chlorophenyl)-3-(2-furyl)-2-propenenitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a flask was added 22.65 g. (0.15 mole) of 4-chlorobenzyl cyanide in 75 ml. of methanol and 14.4 g. (0.15 mole) of 2-furaldehyde in 50 ml. of methanol. While stirring at room temperature, 12.0 g. (0.15 mole) of aqueous 50% sodium hydroxide was added dropwise. Within 30 minutes, a precipitate formed and 50 ml. of additional methanol was added. After one hour, the solid was filtered and dried to give 27.5 g. (91.2% yield) of 2-(4-chlorophenyl)-3-(2-furyl)acrylonitrile as a light yellow solid.

Workup

  1. additionTo a flask was added 22.65 g
  2. customa precipitate formed
  3. waitAfter one hour
  4. filtrationthe solid was filtered
  5. customdried
  6. customto give 27.5 g

Sources & evidence

ORD record
ord-aede02a79b384faebda9b0d4d3c8ef26
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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