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Author: Subject: Ephedrine from Propiophenone...
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shocked.gif posted on 6-4-2017 at 14:35

Quote: Originally posted by Melgar  

Wait... this is an isonitroso compound, not a nitro anything. At the end, the one guy says it's reducing a nitroalkene to an amine, which isn't actually true, since it's just a ketoxime, which is what "isonitroso" is an old term for. Oximes, being imines of hydroxylamine, which are apparently far more stable than ordinary imines.

It uses sodium ethoxide though, which basically necessitates that you have metallic sodium. (Which I do, but when coming up with novel synthetic routes, the more OTC the better, IMO) I wonder if aluminum ethoxide would suffice?

Edit: Of course the nitro ester should be distilled freshly in any case.

Nitro esters... you mean like nitroglycerin? Or ethyl nitrate? ;)

[Edited on 3/31/17 by Melgar]

Well, the reduction itself there, I don´t know if this works as advertised. Probably it does on isonitrosoacetophenone as used in this example, but not so likely with our substrate. Anyway!

I would think that an alcoholic solution of KOH/NaOH in dry alcohol, which then does contain some alkoxide, would be worth a try.
So the metallic sodium may not be needed.
However, I used it as I wanted to follow the procedure as close as possible, and it has worked fine, with very satisfying results already on the first attempt.

As for the "nitro ester", please excuse this! :o
It was late and, of course I meant nitrite esters, e.g. isopropyl nitrite, amylnitrite and similar, and not nitrate...
The former was what I´ve used by the way.
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