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

HRID 893414Notes

Reaction equation

HRID 893414 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(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].C[K].N1CCCC[CH2:23]1.C(=O)=O.Cl>C(O)(=O)C.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:15]([O:17][CH3:23])=[O:16]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 691752,4-DimethoxybenzaldehydeHCID 178525632HCID 178525632, compound

Product 1

HCID 54162205Methyl 3-(2,4-dimethoxyphenyl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

A mixture of 105.6 g of 2,4-dimethoxybenzaldehyde, 93.6 g of methyl potassium malonate, 200 ml of pyridine (dried over KOH), 1.2 ml of piperidine, 36 ml of acetic acid and 48 g of 3A molecular sieves is heated at 150° C. until evolution of CO2 has ceased. The solution is poured onto ice while hot, and the mixture is acidified to pH 1-2 with concentrated hydrochloric acid and then stirred in the ice bath for 20 minutes. The precipitate is filtered off with suction, washed with 1N HCl and water and dried.

Workup

  1. additionThe solution is poured onto ice while hot, and the mixture
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with 1N HCl and water
  4. customdried

Sources & evidence

ORD record
ord-1059b7c7016645dcae8dbc833471c11b
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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