2,4,5-Trimethoxybenzaldehyde → alpha-Cyano-3-chloro-2',4',5'-trimethoxystilbene

HRID 1900095Notes

Reaction equation

HRID 1900095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:14]=1[CH:15]=O>C(O)C.[OH-].[Na+]>[C:9]([C:8](=[CH:15][C:14]1[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:13]=1[O:12][CH3:11])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)#[N:10]

Participants

5

Reactant 2

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 73722m-Chlorophenylacetonitrile

Product 1

HCID 54364916alpha-Cyano-3-chloro-2',4',5'-trimethoxystilbeneYield 92.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent

Procedure

3-chlorophenylacetonitrile (purchased from Tokyo Kasei), 1.96 g (10.0 mmol), and 1.96 g (10.0 mmol) of 2,4,5-trimethoxybenzaldehyde (purchased from Lancaster) were dissolved in 10 ml of ethanol (purchased from Kokusan Kagaku) under heating, 2 drops of 20% aqueous sodium hydroxide solution was added to the solution and stirred over night, and the precipitate was crushed, and washed with ethanol twice and hexane twice, and dried to give 3.05 g (yield: 92.5%) of α-cyano-3-chloro-2',4',5'-trimethoxystilbene (as a yellow crystalline).

Workup

  1. temperatureunder heating
  2. customthe precipitate was crushed
  3. washwashed with ethanol twice
  4. dry with materialhexane twice, and dried

Sources & evidence

ORD record
ord-ee7f210cefe74c128fde40c4ff9d2150
Source dataset
uspto-grants-1996_11
Patent number
US05574062

Reaction notes

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