Ibuprofen, (+-)- → Ethenyl alpha-methyl-4-(2-methylpropyl)benzeneacetate

HRID 22071

Reaction equation

HRID 22071 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[C:16](OC=C)(=O)[CH3:17]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([O:14][CH:16]=[CH2:17])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 3672Ibuprofen, (+-)-HCID 7904Vinyl Acetate

Product 1

HCID 21252143Ethenyl alpha-methyl-4-(2-methylpropyl)benzeneacetateYield 82%

Procedure

100 g of 2-(4'-isobutylphenyl)propionic acid (ibuprofen) were taken up in 1 l of vinyl acetate and heated under reflux to boiling in the presence of 2 g of Li2PdCl4 and 20 g of active carbon. The reaction was followed by thin layer chromatography. After 8 hours, the catalyst was filtered off and the filtrate was concentrated to dryness. After filtration through silica gel using hexane:ethyl acetate (10:1), 92.7 g (39.9 mmol; 82%) of vinyl 2-(4'-isobutylphenyl)propionate were obtained as a clear oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated to dryness
  5. filtrationAfter filtration through silica gel

Sources & evidence

ORD record
ord-6059719b4fb74d3ab6d800fed7ca79a4
Source dataset
uspto-grants-1995_06
Patent number
US05426211

Linked notes

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