Carbon Dioxide → Methyl 4-carboxycinnamate

HRID 984029Notes

Reaction equation

HRID 984029 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([O-])=O.[K+].[C:10]([C:13]1[CH:20]=[CH:19][C:16](C=O)=[CH:15][CH:14]=1)([OH:12])=[O:11].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[CH3:8][O:7][C:1]([CH:2]=[CH:3][C:16]1[CH:19]=[CH:20][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)=[O:6]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 2724687Potassium methyl malonate

Product 1

HCID 54440358Methyl 4-carboxycinnamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

18.74 g (0.12 mol) of potassium monomethyl malonate were suspended in 18 ml of pyridine. 15.01 g (0.1 mol) of 4-carboxybenzaldehyde and 0.85 g (0.01 mol) of piperidine were added at room temperature with stirring and the mixture was boiled under reflux until the evolution of carbon dioxide had ceased (about 2 h). A further 60 ml of pyridine were added and the mixture was stirred under reflux for a further 1 h. The reaction mixture was treated with stirring with 500 ml of ice and 110 ml of concentrated hydrochloric acid. After the addition was complete, the mixture was stirred for a further 20 min, and the product was filtered off with suction, washed with water and recrystallized from isopropanol. Yield: 12.85 g (62%).

Workup

  1. custom(about 2 h)
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for a further 1 h
  4. additionThe reaction mixture was treated
  5. additionAfter the addition
  6. stirringthe mixture was stirred for a further 20 min
  7. filtrationthe product was filtered off with suction
  8. washwashed with water
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-873ed80a271f4ddaa3d2cf8c2254ebf2
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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