Carbon Dioxide → 2-Propenoic acid, 3-(4-formylphenyl)-

HRID 1646526Notes

Reaction equation

HRID 1646526 reaction equation
N1CCCCC1.[C:7]1([CH3:15])[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].C(=O)=O>N1C=CC=CC=1>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH:15]=[CH:17][C:18]([OH:20])=[O:19])=[CH:8][CH:9]=1)=[O:14]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 77254-MethylbenzaldehydeHCID 8082Piperidine

Product 1

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-Yield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A drop of piperidine was added to a mixture of 13.4 g of p-tolualdehyde, 5 g of malonic acid and 50 ml of pyridine. The mixture was heated to reflux until evolution of carbon dioxide was discontinued. The reaction mixture was concentrated under reduced pressure and, 200 ml of water and 12 g of hydrogen sodium carbonate were added thereto. The mixture was washed with ethyl acetate and made acidic with conc. hydrochloric acid. The precipitated crystals were taken out by filtration, thoroughly washed with water and dried to give 6.6 g of p-formylcinnamic acid.

Workup

  1. temperatureThe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure and, 200 ml of water and 12 g of hydrogen sodium carbonate
  3. additionwere added
  4. washThe mixture was washed with ethyl acetate
  5. filtrationThe precipitated crystals were taken out by filtration
  6. washthoroughly washed with water
  7. customdried

Sources & evidence

ORD record
ord-954d4e4e2d884d0e92837ca96c673ccc
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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