Malonic Acid → 4-[(E)-2-(4-pyridyl)vinyl]cinnamic acid

HRID 2287592Notes

Reaction equation

HRID 2287592 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20].C(OCC)(=O)C>N1C=CC=CC=1.C(O)C>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[CH:18][C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 867Malonic AcidHCID 8857Ethyl AcetateHCID 53747304-(2-(4-Formylphenyl)ethenyl)pyridine

Product 1

HCID 702455054-[(E)-2-(4-pyridyl)vinyl]cinnamic acidYield 46.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of 4-[(E)-2-(4-pyridyl)vinyl]benzaldehyde (50 mg) in pyridine (0.025 ml) and ethanol (0.075 ml) was added malonic acid (27.4 mg), and the mixture was refluxed for 7 hours. After cooling, ethyl acetate was added thereto, the resulting precipitates were collected by filtration to give 4-[(E)-2-(4-pyridyl)vinyl]cinnamic acid (28 mg).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. temperatureAfter cooling
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1bfb60053e6c41a9995cfa13720026b7
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

Loading…