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+ Inorganic chemistry
Posted by
Nick Kapatais

Hydrochloride Salt Deprotonation

David Quinn  Follow
Right, I meant that (CH3)3COH can destroy the ester same as water will do.

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Bring Back Democracy  Follow
Has anyone tried potassium tert-butoxide?  It's just a thought off the top of my head, and one would have one equivalent of KCl.

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Andrew Yap  Follow
I don't see where the water would come from; it looks as if one mole of tert-butanol would be produced.  There are techniques to desalt amino acids, although I am not sure whether or not they are applicable here.  As for the question of rapid hydrolysis, I suspect that it depends on pH.

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Chuck Smallman  Follow
@Babcock_Hall
Neutralisation with KOC(CH3)3 will yield KCl and water and "ester is rapidly hydrolyzed by water".

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Attah Peter  Follow
I never considered (or handled) tert-butoxides before. That's something to consider, thank you.

I suppose I could also dissolve the ester in solvent, and add 1 eq of TEA (triethylamine), which would presumably yield the free ester and TEA-hcl which could be easily recovered by filtration, basified, and reused. Seems like an elegant solution being able to regenerate/reuse the amine, whereas zinc chloride (or aluminum chloride as suggested) can't be converted back into their respective metallic states with as much ease.

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Bunny97  Follow
Maybe aluminium powder will be stronger reductant.

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