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Chapter 21: Q53P (page 1141)

Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.

Aspirin Acetaminophen

Short Answer

Expert verified

Formation of aspirin

Phenol Acetaminophen

Formation of acetaminophen

Step by step solution

01

Formation of aspirin from phenol

Phenol undergoes acylation in the presenceto form hydroxy benzaldehyde, which then reacts with chromic acid by replacing the aldehyde group with acid, followed by a reaction with acetic acid to give aspirin as the desired product.

Formation of aspirin

02

Preparation of acetaminophen

Phenol reacts withinthe presence ofto form acetaminophen as the desired product which is represented as:

Phenol Acetaminophen

Formation of acetaminophen

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Most popular questions from this chapter

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

k.

l.

m.

n.

o.

p.

q.

r.

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(a)N-ethylbenzamide鈫�benzylethylamine

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

c. PhCONHCH2CH3

Propose a mechanism for the following ring-opening transesterification. Use the mechanism in Problem 21-13 as a model.

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.

(c) phthalic acid monoamide
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