2-(4-Isobutylphenyl)acrylic acid → Ibuprofen, (+-)-

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence