Question

Show how you might prepare the anti-inflammatory agent ibuprofen starting from isobutyl benzene. More than one step is needed.

Short answer

The synthesis of ibuprofen starting from isobutyl benzene can be shown.

Step-by-step solution

Steps for the synthesis of ibuprofen

The acylation of Friedel-Crafts with acetyl chloride in the presence of AlCl₃ which introduces an acetyl group in p-position for the yield of p-isopropylacetophenone. The ketone will convert into secondary alcohol when it is reduced with NaBH₄. There is a displacement of bromine to –OH in the alcohol when it is treated with PBr₃ to yield bromide. The nitrile to bromide conversion when treated with NaCN and hydrolysis will yield ibuprofen.

Structure for the ibuprofen synthesis

The steps for the ibuprofen synthesis have shown below,