Methanol → 3-Hydroxy-4-methoxybenzenepropanoic acid

HRID 1007622

Reaction equation

HRID 1007622 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>O.[C].[Pd]>[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 99.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

3-Hydroxy-4-methoxycinnamic acid (15.0 g, 77.2 mmo) and 10% palladium carbon in the 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 hydrogen atmosphere of normal pressure (0.1 MPa) at 50° C. for 5 hours for reaction. The reaction solution was filtrated to remove the catalyst, and the filtrate 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. filtrationThe reaction solution was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure to solidification

Sources & evidence

ORD record
ord-48c93856764741ffacd57281a88c3f51
Source dataset
uspto-grants-2004_09
Patent number
US06794531B2

Linked notes

Loading…