July 02, 2022, 02:11:03 PM
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Topic: Nitroalkane from nitroalcohol  (Read 357 times)

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Offline Parathormon

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Nitroalkane from nitroalcohol
« 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?

Offline rolnor

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Re: Nitroalkane from nitroalcohol
« Reply #1 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

Offline Parathormon

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Re: Nitroalkane from nitroalcohol
« Reply #2 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…

Offline rolnor

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Re: Nitroalkane from nitroalcohol
« Reply #3 on: April 12, 2022, 01:06:19 PM »
We all have these, no problem!

Offline clarkstill

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Re: Nitroalkane from nitroalcohol
« Reply #4 on: April 13, 2022, 05:13:48 AM »
Form the tosylate and reduce with LiAlH4?

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