Title of project

The Synthesis of Pure (S)- Ibuprofen using a Greener Alternative

Faculty Advisor

James Wollack



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The Synthesis of Pure (S)- Ibuprofen using a Greener Alternative

Ibuprofen is a fever/pain reducer analgesic. In this four step process the most active enantiomer of ibuprofen, (S)-ibuprofen, is isolated from commercially available tablets. This method has been based off of a previous study but a “greener” approach was taken. Racemic ibuprofen was isolated from six over the counter ibuprofen tablets via extraction. Next the racemic ibuprofen is converted to an acid chloride using SOCl2 and treated with triethyl amine to form a ketene. The ketene is then reacted with (S)-ethyl lactate to form a mixture of diastereomers which are separated and saponified to yield pure (S)-ibuprofen. To make the reaction more green , ethly chloroformate will also be substituted for thionyl chloride because it's MSDS reactivity rating is 0, whereas thionyl chloride's reactivity rating is 2. The desired product is pure (S)- ibuprofen. (S)- ibuprofen reportedly works in 12 minutes, whereas racemic Ibuprofen takes 36 minutes to show its full effects in the body.