Talk:Phenyl salicylate

Sorry for the many edits to this article

This article originally attributed the first synthesis of phenyl salicylate to the Polish chemist and doctor Merceli Nencki (1847–1901), who supposedly discovered this compound circa 1883. A number of sources claim this, but none of them cite their original source for this information. There are also sources that claim that Nencki synthesized phenyl salicylate in 1885, but, again, there's no documentation to substantiate that claim.

However, there is documentation that the German chemist Richard Siefert (1861–1919) synthesized it in 1885, and he claimed to have been the first person to have synthesized it.

However, the U.S. patent of 1886 for the preparation Salol — which was a commercial name for phenyl salicylate and which is supposedly a contraction of "SALicylate of phenOL" — includes both Nencki and Siefert. The inclusion of both investigators in the patent suggests that they both had a legitimate claim on Salol.

On the basis of the available evidence, I surmise that Nencki synthesized phenyl salicylate, realized (and investigated) its potential pharmaceutical applications, and therefore didn't publicize his discovery; whereas Seifert didn't realize phenyl salicylate's potential applications — as evidenced by the fact that his 1885 paper devotes little attention to the new compound — and therefore did publish his findings.

I'm making many edits to this article as I unravel the story of this compound.

VexorAbVikipædia (talk) 11:52, 25 April 2020 (UTC)

Here is the story of phenyl salicylate to the best of my understanding:

• Nencki had been studying the chemistry of phenol. (See the "Nencki reaction" (1881).) Phenol had been considered by chemists to be an acid, but Nencki discovered that it could form esters with organic acids. In 1883, he discovered that phenol could form an ester with salicylic acid. Being a doctor, he probably knew that salicylate salts had medicinal value but that they were poorly tolerated by some patients. So he investigated the behavior of phenyl salicylate in the body.
• At some time after 1883 (probably 1884), Nencki was asked by Dr. Sahli whether Nencki knew of a salicylate compound that might be better tolerated by patients. Nencki recommended phenyl salicylate, and the two men began a collaboration to investigate phenyl salicylate's use as a pharmaceutical — with Sahli investigating the clinical applications of phenyl salicylate. From 1883 into 1886, neither Nencki nor Sahli published their findings.
• Meanwhile, Seifert was investigating the chemistry of phenyl esters. During the course of this work, he discovered phenyl salicylate, which he thought was a new compound because Nencki hadn't published his findings.
• Seifert was working under Prof. Schmitt, who was connected with the Heyden corporation. (Schmitt, with the German chemist Kolbe, had discovered a more efficient method of producing salicylic acid, the main product of the Heyden corporation. Schmitt sold the method to Heyden.) Schmitt probably arranged for Seifert to get a job at Heyden in 1885, because Seifert had discovered a new compound of salicylic acid and understood the chemistry of salicylic acid.
• Meanwhile, Schmitt probably learned of Nencki and Sahli's work on phenyl salicylate. Schmitt probably informed the Heyden corporation of Nencki and Sahli's promising pharmaceutical. Hence the Heyden corporation hired Seifert and probably began negotiations with Nencki and Sahli (and Seifert) regarding patents and the commercial use of phenyl salicylate as a pharmaceutical.
• In 1886, Germany gave Nencki and the Heyden corporation a patent for phenyl salicylate, whereas the United States gave a patent to Nencki and Seifert. (French and British patents were also obtained, but I couldn't find them.)
• Meanwhile, in April of 1886 — presumably with patents (almost) secured and negotiations with Heyden concluded — Sahli made a public announcement about Salol at the Berne Society of Medicine and Pharmacy.

VexorAbVikipædia (talk) 14:58, 1 May 2020 (UTC)