58E
Question
Show how you might prepare the anti-inflammatory agent ibuprofen starting from isobutyl benzene. More than one step is needed.
Step-by-Step Solution
Verified Answer
The synthesis of ibuprofen starting from isobutyl benzene can be shown.
1Step 1: 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.
2Step 2: Structure for the ibuprofen synthesis
The steps for the ibuprofen synthesis have shown below,
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