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The synthesis of ibuprofen (1 of 3)

Boots’ method of making ibuprofen described in their patent starts from the compound 2-methylpropylbenzene, (Figure 7).


Figure 7: Structure of 2-methylpropylbenzene.

2-methylpropylbenzene can be made from compounds separated from crude oil and has a similar carbon skeleton to that of ibuprofen.


Figure 8: The first page of the original patent for ibuprofen. (Courtesy of the International Ibuprofen Foundation)
(click to enlarge and see full patent)


Question 6a

What is the only functional group of 2-methylpropylbenzene?

Answer 6a

A benzene ring.

Question 6b

What type of reactions does this functional group usually undergo?

Answer 6b

Electrophilic substitutions.

Question 7a

What extra functional group does ibuprofen have compared with 2-methylpropylbenzene?

Answer 7a

A carboxylic acid.

Question 7b

What sorts of reactions can be used to prepare this functional group?

Answer 7b

Oxidation of primary alcohols and aldehydes, hydrolysis of nitriles, hydrolysis of acid derivatives such as acid chlorides, esters, and amides.