Ethyl Acetate → 3-Hydroxy-4-methoxybenzenepropanoic acid

HRID 2101080Notes

Reaction equation

HRID 2101080 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CCOC(C)=O.[H][H]>[Pd].CO>[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 27520543-Hydroxy-4-methoxybenzenepropanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid (3 g), 10% Pd/C (0.5 g), EtOAc (50 ml) and MeOH (50 ml) was shaken in Parr apparatus for 5 hs under 30-40 psi of hydrogen. Then the solution was passed through a celite pad and was concentrated to give 3-(3-Hydroxy-4-methoxy-phenyl)-propionic acid (3 g). LC-MS: m/e 197 (MH+).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-fd7021e472c043e790cd21ded5cbb233
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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