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Chapter 17: Q12P (page 543)

How would you carry out the following transformation, a step used in the commercial synthesis of (S)-ibuprofen?

Short Answer

Expert verified

The transformation occurs in the commercial synthesis of (S)-ibuprofen is,

Step by step solution

01

Conversion of alcohols into Tosylates

The SN2 reaction of alcohol via a tosylate occurs with only one inversion, and the stereochemistry of the product has the opposite stereochemistry to the starting alcohol compound.

02

The commercial synthesis of (S)-ibuprofen

We know that the reactions which run under SN2conditions have OH as a poor leaving group. The p-TosCl is an excellent leaving group, and the reaction of toluenesulfonate of alcohol with CN-occurs rapidly under SN2conditions. This gives the desired product with the inversion of configuration at the chiral carbon.

Synthesis of (S)-ibuprofen

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Most popular questions from this chapter

Reduction of 2-butanone with NaBH4yields 2-butanol. Is the product chiral? Is it optically active? Explain.

What alcohols would give the following products on oxidation?

(a)

(b)

(c)

Question:For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.

a)

b)

c)

What products would you expect from oxidation of the following compounds with CrO3 in aqueous acid? With the Dess-Martin periodinane?

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  2. 2-Hexanol
  3. Hexanal

p-Nitrobenzyl alcohol is more acidic than benzyl alcohol, but p-methoxy-benzyl alcohol is less acidic. Explain.
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