4-Cyanobenzaldehyde → HCID 53888350, compound

HRID 1586211Notes

Reaction equation

HRID 1586211 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].[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16]>CO>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[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:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 802223-AcetylbenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 53888350HCID 53888350, compoundYield 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 (0.987 gm, 6.8 mmol) and 4-cyanobenzaldehyde (0.891 gm, 6.8 mmol) in dry methanol. Within 5 minutes, a precipitate began to form. The mixture was stirred at room temperature for 4 hrs and diluted with methanol. The solids were filtered off, washed with cold methanol and dried to give 3-[3-(4-cyanophenyl)-1-oxo-2-propenyl]benzonitrile as a white solid 1.7 gm (97%). MS: (M+H)+ 259; 1H NMR (CDCl3): 7.55 (d, 1H), 7.65 (t, 1H), 7.75 (s, 4H), 7.85 (m, 2H), 8.25 (d, 1H), 8.30 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-014c3cb8527c453b8d3ffdea0cc8e08f
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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