Charles Darwin University

PHAR 305

Mikayla Pene, s301402
PHA212 Medicinal Chemistry, Practical Assessment 2
Synthesis of Common Analgesic, Paracetamol
Aim
To produce the common analgesic, paracetamol, by a single-step synthesis starting with
para-aminophenol.
Introduction
Acetaminophen (paracetamol) is a pharmacologically active compound belonging to two
drug classes, analgesics and antipyretics. Analgesics are compounds that are used to reduce
pain, whereas antipyretics are used to reduce fever[Omu17]. Acetaminophen is a weak
inhibitor of the prostaglandins in the brain; the chemicals that cause inflammation and
swelling. The drug relieves fever through its action on the hypothalamus (heat regulating
gland) of the brain[Gra05]. Acetaminophen consists of a benzene ring centre, replaced by
one hydroxyl group and the nitrogen atom of an amide group in the para (1,4) sequence.
4-aminophenol, also known as hydroxyl-aniline, is an organic compound commonly used in
the synthesis of pharmaceuticals. The compound is one of the three isomeric aminophenols;
2-aminophenol and 3-aminophenol are the remaining two isomers. By treating it with acetic
anhydride, an amide bond is produced from acetylation as shown below:
C6H7NO + C4H6O3  C8H9NO2 + C2H4