Ibuprofen, (+-)- → Ethenyl alpha-methyl-4-(2-methylpropyl)benzeneacetate
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
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
- temperatureheated
- temperatureunder reflux
- filtrationthe catalyst was filtered off