Phenyl salicylate, or salol, is the organic compound with the formula C6H5O2C6H4OH. It is a white solid. It is occasionally used in sunscreens and as an antiseptic.

Production and reactions

The title compound was synthesized first in 1883 by the Polish chemist and doctor Marceli Nencki (who didn't publish his findings) and then independently in 1885 by the German chemist Richard Seifert (de) (1861–1919) (who did publish his findings). It is synthesized by heating salicylic acid with phenol in the presence of phosphoryl chloride. It also arises from heating salicylic acid: The conversion entails dehydration and decarboxylation. Heating phenyl salicylate in turn gives xanthone. In this conversion, phenol is produced as well as carbon dioxide.

Salol reaction

In the salol reaction, phenyl salicylate reacts with o-toluidine in 1,2,4-trichlorobenzene at elevated temperatures to the corresponding amide o-salicylotoluide. Salicylamides are a type of drug.

Medical

It has been used as an antiseptic based on the antibacterial activity upon hydrolysis in the small intestine. It acts as a mild analgesic.

History

The Swiss physician Hermann Sahli (sometimes spelled "Saly") (1856–1933) sought a substitute for sodium salicylate, which was used as a treatment for rheumatoid arthritis but which wasn't tolerated by some patients. So Dr. Sahli asked the Polish chemist and doctor Marceli Nencki of Bern, Switzerland, if he knew of a salicylate compound that lacked sodium salicylate's side effects. See: