Does anyone know how to synthesize ibuprofen from benzene?

Question

I can use any reagents or reactions that are normally used in a Organic Chemistry I or II college course.

Answer 1

C6H6 + (CH3)2CHCOCl + AlCl3 → (CH3)2CHCOC6H5 (1)

Freidel - Crafts acylation. Akylation will not work here because the cation will rearrage to t-butyl instead of the needed isobutyl group.

(1) + Zn/Hg/HCl → (CH3)2CHCH2C6H5 (2)

Clemmenson reduction of ketone to methylene.

(2) + CH3COCl + AlCl3 → (CH3)2CHCH2C6H4COCH3 (3)

Freidel - Crafts acylation, para placement predominates.

(3) + LiAl4 → (CH3)2CHCH2C6H4CH(OH)CH3 (4)

LAH reduction of ketone to alcohol.

(4) + SOCl2 → (CH3)2CHCH2C6H4CHClCH3 (5)

Thionyl chloride Cl substitution of hydroxyl.

(5) + Mg → (CH3)2CHCH2C6H4CHMgClCH3 (6)

Production of Grignard.

(6) + CO2 → (CH3)2CHCH2C6H4C*H(COOH)CH3 (ibufrofen)

Reaction of Grignard with dry ice, & acid workup.

The final product will have an asymmetric center (the C with the *). This synthesis will produce a racemic mixture. However, apparently the body can change the chirality of the wrong stereoisomer to the correct stereoisomer.