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Topic: How to remove a primary hydroxyl group  (Read 5394 times)

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Offline CrimpJiggler

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How to remove a primary hydroxyl group
« on: October 23, 2013, 09:31:11 AM »
I'm looking for a way to dehydroxylate secondary carbons. For example, something like this:

how could I get rid of that hydroxy group, while leaving the ethyl group intact? I read about some electrochemical methods, but they seem a bit above my head in terms of the setup needed.

Offline Archer

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Re: How to remove a primary hydroxyl group
« Reply #1 on: October 23, 2013, 09:39:06 AM »
Have you got any ideas, other than electochemistry?

What is the chang in the oxidation state going from CH2-OH to CH3?
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Offline srivarey

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Re: How to remove a primary hydroxyl group
« Reply #2 on: October 31, 2013, 03:18:50 AM »
one of the most common methods of deoxygenating an alcohol

http://en.wikipedia.org/wiki/Barton%E2%80%93McCombie_deoxygenation

Offline cbn

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Re: How to remove a primary hydroxyl group
« Reply #3 on: October 31, 2013, 10:34:57 AM »
you can try acid catalyst for making alkene (-OH.... =) and then you can convert alkene to alkane by using hydrogenation method.

Offline spirochete

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Re: How to remove a primary hydroxyl group
« Reply #4 on: October 31, 2013, 12:47:30 PM »
You could do something that exploits the greater acidity of the O-H relative to NH2. Perhaps one equivalent of NaH to deprotonate (this can be tricky in the real world because NaH is not so soluble so maybe use a different base) and then functionalize the alkoxide into a tosylate, eliminate with bulky base, then hydrogenate.

I am not sure if deprotonating first is even necessarsry, but I am not sure if the NH2 would too nucleophilic to selectively tosylate an alcohol in its presence. Making an alkoxide I figured would solve this problem.

This is the "sophomore" level organic chem. There is probably a better way to do it in real life if that's what you're going for. Search for "remove primary hydroxyl in the presence of primary amine" or something like that on sci finder, or even do a structure search.

Offline discodermolide

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Re: How to remove a primary hydroxyl group
« Reply #5 on: October 31, 2013, 12:50:22 PM »
I would be tempted to convert it to a thioether and use Raney nickel.
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