3-Acetylbenzonitrile → 3,3'-Dicyanochalcone

HRID 1586222Notes

Reaction equation

HRID 1586222 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)#[N:13]>CCl>[C:12]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:2][C:1]([C:4]2[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=2)[C:7]#[N:8])=[O:3])[CH:19]=[CH:20][CH:21]=1)#[N:13]

Participants

4

Reactant 2

HCID 802223-AcetylbenzonitrileHCID 90670m-Formylbenzonitrile

Product 1

HCID 544082233,3'-DicyanochalconeYield 16.2%

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

Part A. 3-acetylbenzonitrile (1 gm, 6.8 mmol) and 3-cyanobenzaldehyde (2.76 gm, 17 mmol) are dissolved in a minimal amount of methyl chloride and 20 g of basic alumina was added. The resulting slurry was vigorously stirred at room temperature for 72 hrs. The slurry was filtered and the filter cake thoroughly washed with methylene chloride. The solvent was removed under vacuum and the residue chromatographed on silica gel eluting methylene chloride to give 3-[3-(3-cyanophenyl)-1-oxo-2-propenyl]benzonitrile as a solid 0.285 gm (15%). MS: (M+H)+ 259; 1H NMR (CDCl3): 7.6 (t, 2H), 7.7 (m, 2H), 7.85 (m, 3H), 7.95 (s, 1H), 8.25 (d, 1H), 8.35 (s, 1H).

Workup

  1. additionwas added
  2. filtrationThe slurry was filtered
  3. washthe filter cake thoroughly washed with methylene chloride
  4. customThe solvent was removed under vacuum
  5. customthe residue chromatographed on silica gel
  6. washeluting methylene chloride

Sources & evidence

ORD record
ord-1d7b2d54cc1943aa9602567dad250f0a
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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