Methanol → 3-Hydroxy-4-methoxybenzenepropanoic acid

HRID 2414990Notes

Reaction equation

HRID 2414990 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].CO>[Pd].O>[OH:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid

Product 1

HCID 27520543-Hydroxy-4-methoxybenzenepropanoic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

3-hydroxy-4-methoxycinnamic acid (15.0 g, 77.2 mmol) and 10% palladium on activated carbon having a water content of 50% (2.26 g) were added to a mixed solvent (330 ml) of methanol and water (Mixing Ratio of 10:1 v/v), and the mixture was stirred under a hydrogen atmosphere of ordinary pressure (0.1 MPa) at 50° C. for 5 hours for reaction. The obtained reaction solution was filtrated to remove the catalyst, and the filtrate obtained was concentrated under reduced pressure to solidification to obtain 3-(3-hydroxy-4-methoxyphenyl)propionic acid (15.1 g, 76.7 mmol, yield: 99%).

Workup

  1. customThe obtained reaction solution
  2. filtrationwas filtrated
  3. customto remove the catalyst
  4. customthe filtrate obtained
  5. concentrationwas concentrated under reduced pressure to solidification

Sources & evidence

ORD record
ord-6405e77b69124cc7ad5cec9a8996556b
Source dataset
uspto-grants-2004_11
Patent number
US06818243B2

Reaction notes

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