ChemistryForever
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Reduction of organic acids without hydrides
As the title says, how can I reduce organic acids without hydrides? They are both expensive and hard to find ...
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Tsjerk
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Reduce to what? Aldehyde, alcohol, alkane? Is your acid substituted? Without details no one can give an answer.
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WGTR
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If we're talking about an organic acid like ethanoic acid, then heating the calcium or lithium salt can produce some acetone, which can then be
reduced via hydrogenation to isopropanol in a tube furnace. Acetone can supposedly be reduced all the way to propane electrochemically, on a cadmium
cathode. The combined efficiencies are probably not that great.
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clearly_not_atara
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WGTR: but you get a dimer!
If you form the ester you can reduce the acids to alcohols with sodium in ethanol.
If you form the nitrile you can reduce to the aldehyde with SnCl2/HCl in diethyl ether followed by hydrolysis.
If you form the aldehyde you can reduce to the alkane with hydrazine/KOH in ethylene glycol.
That should about cover it, I think.
[Edited on 04-20-1969 by clearly_not_atara]
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JJay
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How does calcium formate react with other calcium carboxylates at high temperatures?
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draculic acid69
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Will ethyl acetate when reduced with NaOet yield 2 moles of ethanol from 1 mole ethyl acetate?
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clearly_not_atara
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NaOEt is not a reducing agent. Sodium metal in alcohol generates electrons.
Aldehyes are produced in low yield IIRC. Formaldehyde is also produced.
[Edited on 16-12-2018 by clearly_not_atara]
[Edited on 04-20-1969 by clearly_not_atara]
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I_love_Diethylether
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I was also wondering about reduction of Esters without hydrides. I didnt find anything good tho, however it is possible to reduce Aldehydes with water
and precipitated Nickel to alcohols. An interesting review to read about this is linked.
Source: Kazuo Hata , Izumi Motoyama & Koji Sakai (1972) THE URUSHIBARA
HYDROGENATION CATALYSTS A REVIEW, Organic Preparations and Procedures International,
4:4, 179-209, DOI: 10.1080/00304947209355544
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Σldritch
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I have never heard of anyone doing it but from my understanding of the Clemmensen reduction mechanism should it not yield a primary alcohol?
[Edited on 16-12-2018 by Σldritch]
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