Hydrochloric Acid → 4-[2-(Methoxycarbonyl)ethyl]cinnamic acid

HRID 2227493Notes

Reaction equation

HRID 2227493 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=O.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.Cl>N1C=CC=CC=1>[CH3:12][O:11][C:9]([CH2:8][CH2:7][C:6]1[CH:13]=[CH:14][C:3]([CH:1]=[CH:16][C:17]([OH:19])=[O:18])=[CH:4][CH:5]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 11063253Methyl 3-(4-formylphenyl)propanoate

Product 1

HCID 538622044-[2-(Methoxycarbonyl)ethyl]cinnamic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 4-formylhydrocinnamate (2.30 g), malonic acid (2.50 g) and piperidine (0.1 ml) in 12 ml pyridine was stirred at 100° C. for 2 hours, and subsequently at 140° C. for 2 hours. After addition of 100 ml ice-cold water, 210 ml of 0.5 mol/l hydrochloric acid was added dropwise to the reaction mixture to precipitate a solid, which was then filtered, washed with water, and dried by heating under reduced pressure to give 4-[2-(methoxycarbonyl)ethyl]cinnamic acid (2.38 g, 84%) as a colorless solid.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. customto precipitate a solid, which
  3. filtrationwas then filtered
  4. washwashed with water
  5. customdried
  6. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-99f90f6d9c4348c8adc592616228d81e
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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