Phenyl salicylate, or salol, is a chemical substance, which was synthesized first in 1883 by the Polish chemist and doctor Marceli Nencki and then independently in 1885 by the German chemistRichard Seifert . It is synthesized by heating salicylic acid with phenol. Once used in sunscreens, phenyl salicylate is now used in the manufacture of some polymers, lacquers, adhesives, waxes, and polishes. Commonly it is used in school laboratory demonstrations on how cooling rates affect crystal size in igneous rocks. Can be used to demonstrate seed crystal selectiveness. Salol is also used as an internal antiseptic and as a mild analgesic..
Salol reaction
In the salol reaction, phenyl salicylate reacts with o-toluidine in 1,2,4-trichlorobenzene at elevated temperatures to the corresponding amideo-salicylotoluide. Salicylamides are one type of drug.
The Swiss physician Hermann Sahli 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 Nencki knew of a salicylate compound that lacked sodium salicylate's side effects. Nencki recommended phenyl salicylate, which he had synthesized circa 1883. While Nencki had been investigating how phenyl salicylate behaved in the body, he hadn't published his findings. Meanwhile, the German chemist Richard Seifert , a student of the German chemist Rudolf Wilhelm Schmitt , independently synthesized phenyl salicylate in 1885. In 1885, Seifert accepted a position at the Heyden chemical corporation of Radebeul, Germany, which manufactured salicylic acid. The United States granted to Nencki and Seifert a patent for the production of phenyl salicylate, whereas Germany granted a patent for its production to Nencki and the Heyden corporation. The Heyden company subsequently sold phenyl salicylate as a pharmaceutical, under the commercial name "Salol", a contraction of "SALicylate of phenOL". Among other applications, Salol was used as an orally administered antiseptic for the small intestine, where the compound is hydrolyzed into salicylic acid and phenol.
