4-Nitrobenzaldehyde → 3-[3-(4-Nitrophenyl)-1-oxo-2-propenyl]benzonitrile

HRID 1586217Notes

Reaction equation

HRID 1586217 reaction equation
C[O-].[Na+].[C:4]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])(=[O:6])[CH3:5].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16]>CO>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[O:6])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 802223-AcetylbenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 542130173-[3-(4-Nitrophenyl)-1-oxo-2-propenyl]benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Part A. Sodium methoxide (25% in MeOH, 1.5 mL, 6.8 mmol) was added dropwise to a solution of 3-acetylbenzonitrile (987 gm, 6.8 mmol) and 4-nitrobenzaldehyde (1 gm, 6.8 mmol) in dry methanol. Within 5 minutes, a precipitate begins to appear. The mixture was stirred at room temperature for 4 hours and diluted with methanol. The solids were filtered off, washed with cold methanol and dried to give 3-[3-(4-nitrophenyl)-1-oxo-2-propenyl]benzonitrile as a white solid 1.7 gm (97%) MS: 279(M+H)+ ; 1H NMR (CDCl3): 7.60 (d, 1H), 7.70 (t, 1H), 7.85 (m, 4H), 8.25 (m, 4H)

Workup

  1. filtrationThe solids were filtered off
  2. washwashed with cold methanol
  3. customdried

Sources & evidence

ORD record
ord-36229b1195c84ad8bb2594b81afe419c
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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