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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Parathormon on April 09, 2022, 11:27:46 PM

Title: Nitroalkane from nitroalcohol
Post by: Parathormon on April 09, 2022, 11:27:46 PM
Hello guys,


Please tell me how can I dehydroxylate the nitroalcohol to not break nitro group and lead to nitroalkane in 85-100% yield?

Catalytic hydrogenation would probably reduce nitro group , due to its non-selectivity, especially that NO2 is more prone to hydrogenation than OH

I thought about Nagai method but theese harsh conditions - dont they impact the yield by some dimeric byproducts coupling somehow my nitroalcohol molecules in pairs?

Ive never seen in literature such an example, beside one patent of DOW chemicals where such a thing is done but with not so high yield and present some byproducts (I think because of hydrogen atmosphere used in those examples)


Maybe there is some other method to do this?
Title: Re: Nitroalkane from nitroalcohol
Post by: rolnor on April 10, 2022, 02:11:32 AM
There is no such thing as 100% yield.
This could be a method:

https://en.m.wikipedia.org/wiki/Barton%E2%80%93McCombie_deoxygenation
Title: Re: Nitroalkane from nitroalcohol
Post by: Parathormon on April 11, 2022, 07:46:34 PM
Thank You very much for Your answer..


Regarding 100% yield, look, I am quite an experienced chemist so you could also assume that this was a mental shortcut…
Title: Re: Nitroalkane from nitroalcohol
Post by: rolnor on April 12, 2022, 01:06:19 PM
We all have these, no problem!
Title: Re: Nitroalkane from nitroalcohol
Post by: clarkstill on April 13, 2022, 05:13:48 AM
Form the tosylate and reduce with LiAlH4?