Acetic Acid → HCID 54411964, compound

HRID 987248Notes

Reaction equation

HRID 987248 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:27][CH2:28][CH3:29])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)[CH:8]=1)[CH3:2].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:20][CH:21]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86595059HCID 86595059, compound

Product 1

HCID 54411964HCID 54411964, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Ethoxy-3-{3-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester (3.69 g; 8.50 mmole) was hydrogenated for 3.5 hours at atmospheric pressure in ethyl acetate (70 ml) and acetic acid (0.5 ml) using Pd/C as catalyst and then filtered through hyflo. The solvent was evaporated in vacuo, dichloromethane and water were added and the phases were separated. The organic phase was dried (sodium sulfate), filtered and evaporated in vacuo to give 3.45 g (yield 93%) of 2-ethoxy-3-{3-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. filtrationfiltered through hyflo
  2. customThe solvent was evaporated in vacuo, dichloromethane and water
  3. additionwere added
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-aee19a55052b4053ad864903431f9564
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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