4-Cyanobenzaldehyde → HCID 53694269, compound

HRID 745253Notes

Reaction equation

HRID 745253 reaction equation
[Br-].C1(=O)[N:6]([CH2:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:10][CH:9]=2)[C:5](=[O:34])[C:4]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:3]12.[CH3:40][O-:41].[Na+].[C:43]([C:45]1[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=1)#[N:44]>CO>[C:5]1(=[O:34])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH:12]=[CH:49][C:48]3[CH:51]=[CH:52][C:45]([C:43]#[N:44])=[CH:46][CH:47]=3)=[CH:32][CH:33]=2)[C:40](=[O:41])[C:35]2=[CH:36][CH:37]=[CH:38][CH:3]=[C:4]12

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 10942334Sodium MethoxideHCID 23315145HCID 23315145, compound

Product 1

HCID 53694269HCID 53694269, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into 800 ml of anhydrous methanol, was dissolved 35.5 g of 4-phthalimidomethylbenzyltriphenylphosphonium bromide. To the resulting solution, through which argon had been passed with stirring for 5 minutes, was added at room temperature slowly dropwise 11.6 ml of anhydrous methanol containing 28% of sodium methoxide. After 10 minutes, 7.9 g of p-cyanobenzaldehyde was added to the reaction mixture and the mixture was stirred at room temperature for 15 hours. The precipitated crystals were collected by filtration to obtain 15.4 g of 4-[2-(4-phthalimidomethylphenyl)ethenyl]benzonitrile.

Workup

  1. waitAfter 10 minutes
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-cdc3888391ee4fbca9f4d39c8bc52acd
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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