Carbon Dioxide → Ethyl 3-(2,4-dimethoxyphenyl)prop-2-enoate

HRID 893411Notes

Reaction equation

HRID 893411 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14]C([O-])=O.N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[CH:14][C:13]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 691752,4-DimethoxybenzaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 53804800Ethyl 3-(2,4-dimethoxyphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

83 g of 2,4-dimethoxybenzaldehyde and 66 g of monoethyl malonate are dissolved in 100 ml of dry pyridine and, after addition of 1 ml of piperidine and 40 g of molecular sieves, refluxed until evolution of CO2 has ceased. The reaction mixture is cooled and then poured onto crushed ice, and the pH is adjusted to 1-2 with concentrated hydrochloric acid, while stirring. Stirring is continued for 20 minutes, and the product which has separated out is filtered off with suction, washed with 1 N hydrochloric acid and water and dried in a desiccator. Yield: 100.2 g, melting point 58° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured
  3. customonto crushed ice
  4. stirringStirring
  5. customthe product which has separated out
  6. filtrationis filtered off with suction
  7. washwashed with 1 N hydrochloric acid and water
  8. customdried in a desiccator

Sources & evidence

ORD record
ord-a3598c69ec1d4813bbbe450d55e3bb2e
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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