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could DMT-oxide-fumarate be reduced directly using zinc and fumaric as the acid instead of acetic?

drpotato

Established member
So, my latest extract had an enormous amount of dmt-oxide, the product is practically an oil, and a very brown one at that. I realized a short while ago that i left the pressure cooked glass bottle sitting on my bench for a few weeks before eventually extracting, and apparently that has the potential to oxidize it pretty bad. and then also after FASA/FASI, i got, not goo, but oil.


Anyway it occured to me that, if zinc could reduce dmt oxide fumarate, that would be really quite convenient, without having to re-salt as the acetate.
is this perhaps the case? i wasnt clear on, if it could, or if acetate/HCl are the only ones documented where it had been done?
would any acid work?

-edit- i have been told that, working or not aside, acetic acid is used since its easy to provide a molar abundance of it, which isnt practical for fumaric acid.
so now i get to thinking, since acetic is weaker, and the presence of an acid is still required, what if right before you basify your DMT-fumarate containing some oxide, you added acetic acid in place of the dissolving water, along with zinc, and then basified after that reaction had taken place. it would consume more carbonate sure but the outcome would be more or less the same, assuming that the ion does not need to match the acid supporting the reaction, my understanding is that the mechanism is due to the dissolving zinc ions, so, i dont see how the salt ion should impact it, provided its still dissolved either way
 
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@Loveall showed that the acidification is more relevant than the dissolving zinc, and that DMT-N-oxide is very likely not involved in this oily material. Rather, it is to do with polymorphs and oligomers. The oligomers get broken down on acidification.

The oxide will be protonated at pH of about 4.5 and below, but amine oxides are fairly water-soluble as 12-carbon molecules anyhow. Amine oxide - Wikipedia

Voluminous zinc oxide waste is a pain in the ass and will eat more of your yield than you'll "recover" from your "oxide".
 
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