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Starting with benzene and using any other

Chapter 21, Problem 21.74

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QUESTION:

Starting with benzene and using any other reagents of your choice, devise a synthesis for acetaminophen: Acetaminophen (Tylenol) N HO O H

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QUESTION:

Starting with benzene and using any other reagents of your choice, devise a synthesis for acetaminophen: Acetaminophen (Tylenol) N HO O H

ANSWER:

Step 1 of 3

Starting with benzene, treatment with molecular chlorine and aluminum trichloride (which acts as a catalyst) forms chlorobenzene. Nitration of this intermediate using a mixture of nitric and sulfuric acids gives the desired para-substituted 1-chloro-4-nitrobenzene. This is the critical intermediate needed for the nucleophilic aromatic substitution reaction.

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