3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester → Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 1861533Notes

Reaction equation

HRID 1861533 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[H][H]>[Pd].O1CCOCC1>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 110779683-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester2×HCID 178418361HCID 178418361, compound

Product 1

HCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of racemic ethyl 2-ethoxy-3-(4-benzyloxyphenyl)propionate of the formula (12a) (40 g) obtained according to the procedure described in step (iv) above, 5% Pd/C catalyst (8 g) and 1,4-dioxane (200 ml) was subjected to hydrogenation at room temperature and 50-60 psi of hydrogen pressure for a period of 8-12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was filtered off and the solvent was removed under reduced pressure,to afford the title compound of the formula (13a) (28-29 g, 97-98%).

Workup

  1. customobtained
  2. customwas subjected to hydrogenation at room temperature
  3. customAfter completion of the reaction
  4. filtrationthe catalyst was filtered off
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a4fe80aeba304bb38e5a46dba6b47c98
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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