an acetylated form of salicylic acid (1-hydroxybenzoic acid), used extensively as a medicinal drug; r.d. 1.4; m.p. 138–140°C; b.p. 140°C (with decomposition). It was first marketed in 1899 as a analgesic. The acid can be obtained from willow bark and it has long been known that the bark could be used for pain relief and for the reduction of fever. The name salicylic acid comes from the botanical name of the willow (Salix alba). Aspirin acts by suppressing the production of certain hormones (prostaglandins and thromboxanes) by inhibiting the enzyme cyclooxygenase (COX). Consequently, it is known as a ‘COX inhibitor’. It is used for the treatment of arthritis and to reduce body temperature. It also acts as an anticoagulant in the blood and small doses are taken regularly to reduce the risk of heart attack. A common side effect of high doses is stomach bleeding and stomach ulcers. Aspirin is made industrially from phenol, which with concentrated sodium hydroxide and carbon dioxide gives sodium phenoxide:
The phenoxide ion undergoes electrophilic substitution to give sodium salicylate:
With acid, this forms salicylic acid, which can be acetylated in the ortho position with ethanoic anhydride.