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

HRID 1861550Notes

Reaction equation

HRID 1861550 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].O1CCCC1>[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 8028TetrahydrofuranSolvent

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 (v) above, 5% Pd/C catalyst (8 g) and tetrahydrofuran (120 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-ceaafed7f97943f7aeacddb923b62699
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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