Ethanol → 3-(4-Hydroxyphenyl)-2-phenoxypropanoic acid methyl ester

HRID 987323Notes

Reaction equation

HRID 987323 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][CH:7]=1.C(O)C>C(OCC)(=O)C.[Pd].[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:27])[CH:4]([O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 111322013-(4-Benzyloxyphenyl)-2-phenoxypropanoic acid methyl ester

Product 1

HCID 178401663-(4-Hydroxyphenyl)-2-phenoxypropanoic acid methyl esterYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Benzyloxyphenyl)-2-phenoxypropanoic acid methyl ester (0.47 g; 1.3 mmole) was hydrogenated in ethyl acetate (20 ml) using Pd/C (18 mg; 5%) as catalyst at atmospheric pressure and room temperature for 23 hours. As the reaction was very slow, the catalyst was changed to palladium hydroxide, ethanol (95%, 10 ml) was added and the pressure was raised to 4 bar. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to give 0.34 g (yield 95%) of 3-(4-hydroxyphenyl)-2-phenoxypropanoic acid methyl ester.

Workup

  1. customat atmospheric pressure and room temperature
  2. customfor 23 hours
  3. additionwas added
  4. temperaturethe pressure was raised to 4 bar
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-de8ab7063fca4ae5ae215ada60e3e7bf
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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