Methyl cyanoacetate → 2-Cyano-3-(3,4-dimethoxyphenyl)prop-2-enoic acid

HRID 1614114Notes

Reaction equation

HRID 1614114 reaction equation
[OH-].[Na+].[C:3]([CH2:5][C:6]([O:8]C)=[O:7])#[N:4].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:15]=O>Cl>[C:3]([C:5](=[CH:15][C:14]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:12]([O:11][CH3:10])[CH:13]=1)[C:6]([OH:8])=[O:7])#[N:4]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 8419VeratraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 6162612-Cyano-3-(3,4-dimethoxyphenyl)prop-2-enoic acidYield 55.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
85 °C

Procedure

To 150 ml of an aqueous solution of 9.19 g of sodium hydroxide, 20.50 g of methyl cyanoacetate was added and, under stirring, 25.38 g of 3,4-dimethoxybenzaldehyde was further added, followed by heating at 85° C. for 40 hours under stirring. After completion of the reaction, the reaction mixture was added to 50 ml of 12 N hydrochloric acid to recover the resultant solid. The solid was repeated twice to recrystallize from ethanol to obtain 19.84 g of the desired compound.

Workup

  1. stirringunder stirring
  2. customAfter completion of the reaction
  3. customto recover the resultant solid
  4. customto recrystallize from ethanol

Sources & evidence

ORD record
ord-cd75f050283a47db9aea23f73c6c2ca6
Source dataset
uspto-grants-1993_03
Patent number
US05196147

Reaction notes

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