3-(3-Benzyloxyphenyl)-2-ethoxyacrylic acid ethyl ester → 2-Ethoxy-3-(3-hydroxyphenyl)propanoic acid ethyl ester

HRID 987120Notes

Reaction equation

HRID 987120 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:21][CH2:22][CH3:23])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13]CC2C=CC=CC=2)[CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:22]([O:21][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:24])[CH3:23]

Participants

4

Reactant 1

HCID 540313813-(3-Benzyloxyphenyl)-2-ethoxyacrylic acid ethyl ester

Product 1

HCID 229884442-Ethoxy-3-(3-hydroxyphenyl)propanoic acid ethyl esterYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound (a) (10.4 g; 31.8 mmole) was hydrogenated at atmospheric pressure in ethyl acetate using Pd/C (dry, 10%) as a catalyst. The reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The starting material was not completely consumed, therefore the hydrogenation was repeated to give 7 g (yield 92%) of the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated in vacuo
  3. customThe starting material was not completely consumed

Sources & evidence

ORD record
ord-46c1264684db480aa778486f9d525f25
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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