Methyl 3-Coumarate → Methyl 3-(3-hydroxyphenyl)propionate

HRID 1250114Notes

Reaction equation

HRID 1250114 reaction equation
[CH3:1][O:2][C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1

Participants

4

Reactant 1

HCID 5352910Methyl 3-Coumarate

Product 1

HCID 1512675Methyl 3-(3-hydroxyphenyl)propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (0.31 g) was added to a solution of trans-3-(3-hydroxyphenyl)acrylic acid methyl ester (31.0 g, 17.4 mmol) (prepared as described in Example 6A) in ethyl acetate (30 mL) at room temperature under a nitrogen atmosphere. The mixture was hydrogenated under a balloon pressure for 4 hours. The catalyst was filtered, and the filtrate was concentrated to dryness. Crude 3-(3-hydroxyphenyl)propionic acid methyl ester (3.16 g) was directly used in the next step.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-cc8e888bd06a43008a0086783b8e6524
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

Loading…