(Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester → [Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

HRID 479210Notes

Reaction equation

HRID 479210 reaction equation
[CH2:1]([O:3][C:4](=[O:25])/[C:5](/[O:22][CH2:23][CH3:24])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[CH3:21])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([O:22][CH2:23][CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:21])[CH3:2]

Participants

4

Reactant 1

HCID 68617018(Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester

Product 1

HCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl esterYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(4-benzyloxy-2-methyl-phenyl)-2Z-ethoxy-acrylic acid ethyl ester (1 g, 2.9 mmol) in ethanol (50 ml) was hydrogenated over 10% palladium on charcoal (250 mg) at ambient temperature for 2 h. The catalyst was filtered off and the solvent evaporated under reduced pressure to give 600 mg (2.4 mmol, 81%) of the title compound as yellow liquid which was used in the next stage without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9b0496e7b61f4edb8b229a6d19c820b2
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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