guy
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Reduction of Chlorobutanol
Can Chlorobutanol be reduced in acid to form tert-butyl-alcohol, similar to how nitro groups are reduced to amines?
HO-C(CH3)2-CCl3 + 3Fe + 3H+ ----> HO-C(CH3)3 + 3Fe2+ + 3Cl-
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Shaddy
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May be, who knows. ;)
At least trichloromethyl group can be reduced with Zinc and HCl.
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bbartlog
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Having just tried this, I can say: not easily, at least not with Fe. Chlorobutanol plus NH4Cl plus Fe, in glycol, yields glop. Actually it yields
hydrogen, probably some FeCl2 (based on color), and glop. Probably some sort of amino-glop, since the NH3 from the NH4Cl is still in the flask.
Anyway, I would say stick with zinc or (if you have it, since someone else mentioned it in a newer thread) sodium.
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AndersHoveland
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I read that haloalkanes are reduced to the corresponding alkane by reaction with LiAlH4.
I am assuming that the hydroxyl group would not be reduced. Tert-butyl alcohol is much more resistant to reduction than other alcohols, this is in
fact the reason that tert-butyl alcohol needs to be used in the reaction to make elemental potassium using magnesium.
I'm not saying let's go kill all the stupid people...I'm just saying lets remove all the warning labels and let the problem sort itself out.
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Lambda-Eyde
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What is it with you and not citing sources?
Here:
http://pubs.acs.org/doi/abs/10.1021/ja01191a035
http://pubs.acs.org/doi/abs/10.1021/jo00341a018
Quote: Originally posted by AndersHoveland  | | I am assuming that the hydroxyl group would not be reduced. Tert-butyl alcohol is much more resistant to reduction than other alcohols, this is in
fact the reason that tert-butyl alcohol needs to be used in the reaction to make elemental potassium using magnesium. |
At what point did you elucidate the mechanism by which the synthesis of potassium from KOH+Mg proceeds? AFAIK there's no consensus about that... Also,
I fail to see how metallic potassium reduces a primary alcohol such as methanol any more than it reduces tert-butanol. Both will react to give the
alkoxide and hydrogen.
This just in: 95,5 % of the world population lives outside the USA
Please drop by our IRC channel: #sciencemadness @ irc.efnet.org
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chemrox
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Yes but an unenviable workup follows. Best to find another. H2 + catalyst...
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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experimenter_
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This is an old thread but
potentially useful for people trying to make catalytic potassium ( https://www.sciencemadness.org/whisper/viewthread.php?tid=14... )
May I ask chemrox (or anyone else who knows) what is the "unenviable workup" that follows? Cannot you distill out the tert-butanol or extract with
another solvent? (I presume the reaction is performed in aqueous phase?)
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experimenter_
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One more idea is to dissolve chlorobutanol in a high boiling solvent (e.g. toluene or dioxane), add Mg turnings and then distill the tert-butanol
(distills at 82-83).
According to sources, CHCl3 is reduced to methane by Mg metal in neutral pH conditions. CHCl3 is a building block of chlorobutanol, so it is possible
that this reduction with Mg will work.
If there is interest about this possible way I could add the links to the sources.
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