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chemist1243
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[*] posted on 13-11-2020 at 08:44
reduction with zinc or iron

I want to reduce some nitrovanillin to the amine. Ive heard of zinc and iron dissolved in HCl being used, but I can’t find any procedures on it. Does anyone know at least a basic outline of one of these aromatic nitro group reductions?

Thanks.
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ArbuzToWoda
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[*] posted on 13-11-2020 at 08:46


These reductions can sometimes get a tiny bit messy. I recommend the use of sodium dithionite or thiourea dioxide instead. You should be able to find many situations of the Fe/HCl reduction too though, where did you search? This looks interesting for example: https://www.researchgate.net/publication/274084261_Chemosele...
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monolithic
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[*] posted on 13-11-2020 at 09:23


https://www.sciencemadness.org/whisper/viewthread.php?tid=15... see the link in the first post
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njl
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[*] posted on 13-11-2020 at 09:33


If you insist on using a dissolving metal reduction then that's ok, but I second thiourea dioxide. Very straightforward to use and cheap.
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Chem Science
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[*] posted on 13-11-2020 at 11:45


maybe this post can help http://www.sciencemadness.org/talk/viewthread.php?tid=155164...
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chemist1243
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[*] posted on 13-11-2020 at 12:20


Thanks guys. ill probably update later to tell you how it went. I’m gonna try the Trimethoxynitrostyrene Method that was mentioned. I expect higher than 20% yield because zinc/HCl reductions are known to give crap yeilds on non-aromatic nitro groups.
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Corrosive Joeseph
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[*] posted on 13-11-2020 at 14:16


Quote: Originally posted by chemist1243  
I can’t find any procedures on it.


I find this hard to believe.... Look up the iron and acid reduction of nitrobenzene. AKA the Bechamp reduction.
https://en.wikipedia.org/wiki/Bechamp_reduction



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