Acide paratoluènesulfonique

Today I’m back in the swing of planning out more traditional multi-step organic syntheses, which is something I have’t done in a while.  Of course a major part of that is combing through the literature — and dealing with all the idiosyncrasies that entails.  Right off the bat, I noticed that Reaxys doesn’t play terribly well with Google’s Chrome browser, something I’d never encountered before being a member of the SciFinder tribe.

One of the other considerations of perusing the synthesis literature is deciphering the myriad of acronyms used by authors.  It’s rather inconvenient to type tert-Butyl(chloro)diphenylsilane over and over again, so we’ve usually use “TBDPSCl” for short.  This, and many other short hands are universally known in the field.  And there are whole lists of common ones.  But every once in a while you come across one you’ve never seen before.

Enter “APTS.”  From a paper on synthetic a-galactosylceramides, we see APTS used in combination with benzaldehyde dimethyl acetal to selectively protect the 4 and 6 positions in galactose.  My early morning, caffeine-deprived brain failed to notice the Abbreviations section at the end of the paper and began scouring the internet for traces of APTS used in the chemical literature.  Undeterred, but finding only apartment listings, I noticed the author affiliations — all authors are from non-US institutions, and one in particular from Institut Parisien de Chemie Moleculaire in Paris, France.

Knowing APTS must be some sort of acid catalyst, and having a very broken understanding of the French language, two and two were put together and APTS became acide paratoluènesulfonique, or para-toluenesulfonic acid.

The Wikipedia page for para-toluenesulfonic acid does list “PTSA” as an acronym, but I think I’ve only seen it written “TsOH” or “pTsOH.”

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