Methyl cyanoacetate → 2-Propenoic acid, 2-cyano-3-(3,4-dimethoxyphenyl)-, methyl ester

HRID 1586631Notes

Reaction equation

HRID 1586631 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])#[N:14]>N1CCCCC1.CO>[C:13]([C:15](=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:16]([O:18][CH3:19])=[O:17])#[N:14]

Participants

5

Reactant 2

HCID 7747Methyl cyanoacetateHCID 8419Veratraldehyde

Product 1

HCID 34378732-Propenoic acid, 2-cyano-3-(3,4-dimethoxyphenyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,4-dimethoxybenzaldehyde 4.15 g, 0.025 mol), methyl cyanoacetate (2.48 g, 0.025 mol), methanol (100 mL) and piperidine (10 drops) is heated at reflux for 2 hours. The reaction mixture is then cooled and the product collected by filtration, washed with methanol and dried in air (yield--6.0 g, 97%). The following structure is supported by mass spectrometry: ##STR20## The compound has an absorption maximum at 361 nm in methylene chloride.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationthe product collected by filtration
  5. washwashed with methanol
  6. customdried in air (yield--6.0 g, 97%)

Sources & evidence

ORD record
ord-ab1f691a11d3402d9f7e00a82c33bb9d
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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