4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform, but soluble to extremely soluble in alcohols, ether, and acetone.
4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics.
4-Hydroxybenzoic acid is produced commercially from potassium phenoxide
and carbon dioxide
in the Kolbe-Schmitt reaction
. It can also be produced in the laboratory by heating potassium salicylate
with potassium carbonate
to 240 °C, followed by treating with acid.
The closely related 2-hydroxybenzoic acid is known as salicylic acid
, a precursor to aspirin