4-Methoxybenzaldehyde → HCID 414693, compound

HRID 1032045Notes

Reaction equation

HRID 1032045 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[O:3].[Na+].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=O)=[CH:14][CH:15]=1>[OH-].[Na+]>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[CH:4][C:2](=[O:3])[C:1]([OH:6])=[O:5])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 23662274Sodium pyruvate

Product 1

HCID 414693HCID 414693, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium pyruvate (24.2 g, 0.22 mol) was dissolved in 200 ml 1N aqueous sodium hydroxide at 20° C. To this solution there was added anisaldehyde (27.4 g, 0.20 mol) at 0.2 ml/min. The solution was aged twenty-four hours at 20° C., cooled at 0° C. and acidified with 6N NCl to pH 1.0 while maintaining a temperature of 0° C. The 4-(p-methoxyphenyl)-2-oxo-3-butenoic acid product was then extracted with 500 ml ethyl acetate and isolated as a yellow solid by concentration under vacuum. The yield by HPLC analysis was 88%.

Workup

  1. waitThe solution was aged twenty-four hours at 20° C.
  2. temperaturewhile maintaining a temperature of 0° C
  3. extractionThe 4-(p-methoxyphenyl)-2-oxo-3-butenoic acid product was then extracted with 500 ml ethyl acetate
  4. customisolated as a yellow solid by concentration under vacuum
  5. customThe yield by HPLC analysis

Sources & evidence

ORD record
ord-ac933bc6cd32455ba1de8f8a9b506ecf
Source dataset
uspto-grants-1990_09
Patent number
US04956490

Reaction notes

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