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Sciencemadness Discussion Board » Fundamentals » Organic Chemistry » A new demethylation reagent pair: AlCl3/Thiourea Go To Bottom

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Author: Subject: A new demethylation reagent pair: AlCl3/Thiourea
Siddy
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[*] posted on 30-1-2009 at 23:01


This is a good find, the clean up seems a little complex due to the solubility of the di-phenol product.

If one were to be isolating the product to perform a methylenation reaction on the Catechol, could one not simply add hydroxide while the crude product is still in the DCM/AlCl3 mix - or would the AlCl3 interfere?
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[*] posted on 31-1-2009 at 18:11


Uhh you'd probably end up with a gelatinous mess of Al(OH)3...
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[*] posted on 31-1-2009 at 18:14


The hydroxy-vanillin is not soluble in the 5% aq. layer, nor the DCM layer (the vanillin is though)

Basically you get a solid, filter it out, and re-crystallize it. Not much easier than that.


The tetra-chloroehtane step boosts yields considerably.

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