Acetic Acid → HCID 53659442, compound

HRID 987234Notes

Reaction equation

HRID 987234 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:30])[CH:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:23][CH:24]=2)=[CH:14][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 54369174HCID 54369174, compound

Product 1

HCID 53659442HCID 53659442, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-{4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]benzylidene}malonic acid dimethyl ester (described in Example 10) (2.31 g; 5.32 mmole) was hydrogenated for 2.5 hours at atmospheric pressure in ethyl acetate (140 ml) and acetic acid (5 ml) using Pd/C (0.8 g) as catalyst and then filtered through hyflo. The solvent was evaporated in vacuo, dichloromethane and diluted sodium bicarbonate solution were added and the phases were separated. The organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated in vacuo to give 2.35 g (yield 100%) of 2-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]benzyl}malonic acid dimethyl ester.

Workup

  1. filtrationfiltered through hyflo
  2. customThe solvent was evaporated in vacuo, dichloromethane and diluted sodium bicarbonate solution
  3. additionwere added
  4. customthe phases were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b9cea126ebaf4f3192f5ebe3638e403e
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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