Acetic Acid → HCID 18424794, compound

HRID 622067Notes

Reaction equation

HRID 622067 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6]C(O)=O.[H][H].[C:18]([OH:21])(=[O:20])C>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]([CH3:6])[C:18]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 995252,3-Dimethoxycinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 18424794HCID 18424794, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,3-Dimethoxycinnamic acid (50 g, 0.24 m) was suspended in a mixture of 120 ml of ethanol and 40 ml of glacial acetic acid, then treated with 0.8 g of 10% palladium-on-charcoal. The mixture was warmed on a steam bath before putting on the Paar shaker. Hydrogenation was continued until the uptake of hydrogen stopped (45 minutes). The catalyst was filtered off and the resulting filtrate was evaporated to dryness. The resulting residue solidified on standing. A quantitative yield of the desired 2,3-dimethoxyphenylpropionic acid was isolated.

Workup

  1. temperatureThe mixture was warmed on a steam bath
  2. custom(45 minutes)
  3. filtrationThe catalyst was filtered off
  4. customthe resulting filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9d96b745aba34b7cb32da2eb72befb2c
Source dataset
uspto-grants-1988_09
Patent number
US04769368

Reaction notes

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