2-(4-Isobutylphenyl)acrylic acid → Ibuprofen, (+-)-
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[CH2:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]>[Ru+3].CO>[OH:14][C:12]([CH:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[CH:10][CH:9]=1)[CH3:15])=[O:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 24 °C
Procedure
A 1.05 mmole portion of 2-(4- isobutylphenyl)acrylic acid (UA) was combined with 0.050 mmoles of ruthenium(III) (2,4-pentanedionate) and 30 ml of methanol in a 50-ml Hastelloy C pressure reactor. The reactor was flushed with hydrogen (3×300 psi) and then sealed with 1000 psi hydrogen. After stirring the mixture at 300 rpm for 21 hr at 24° C., a GC analysis of the red solution showed a product composition of 8% ibuprofen and 92% UA. The mixture was then stirred (300 rpm) at 100° C. for 8 hr with 1000 psi H2 to obtain complete conversion of the UA to ibuprofen. HPLC analysis showed the ibuprofen was racemic (0% ee).
Workup
- customThe reactor was flushed with hydrogen (3×300 psi)
- customsealed with 1000 psi hydrogen
- stirringThe mixture was then stirred (300 rpm) at 100° C. for 8 hr with 1000 psi H2
Sources & evidence
- ORD record
- ord-70754b3f10a945ce9be4f6db6f0bfcb0
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05304524
Reaction notes
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