3-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl ester → 2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid methyl ester

HRID 2305318Notes

Reaction equation

HRID 2305318 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([O:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 219309623-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 149239942-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 3-[4-benzyloxyphenyl)-2-ethoxypropanoate (3.7 g, 11.78 mmol; preparation 2) and 10% Pd-C (0.37 g) in ethyl acetate (50 mL) was stirred at 25° C. under 60 psi hydrogen pressure for 24 h. The catalyst was filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using a mixture of ethyl acetate and pet. ether (2:8) as an eluent to afford the title compound (2.2 g, 84%) as an oil.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was chromatographed over silica gel using
  4. additiona mixture of ethyl acetate and pet. ether (2:8) as an eluent

Sources & evidence

ORD record
ord-880a37afa876453aa2d6230c274b3e7f
Source dataset
uspto-grants-2002_08
Patent number
US06440961B1

Reaction notes

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