Sciencemadness Discussion Board

Reducing 2-butanone to 2-butanol

vmelkon - 22-5-2015 at 08:37

Hello,
I was looking into how 2-butanone can be converted into 2-butanol.
Looks like sodium borohydride could be used but I don't have it and it is very expensive. On top of that, I could not produce sodium borohydride.
There is also lithium aluminum hydride but this is also hard to get + expensive + hard to produce.

Are there other substances that could be used?

smaerd - 22-5-2015 at 09:11

Yes, if you don't mind the racemic product. This can be done via electrochemistry. Edit - Zinc electrodes seem to be the way to go 40% yield isn't bad considering how cheap electrons are.

I have an article which I have no idea where I found it, so I will upload it. "THE ELECTROLYTIC REDUCTION OF METHYL ETHYL KETONE TO sec-BUTYL ALCOHOL AND n-BUTANE", SHERLOCK SWANN, JR., R. W. BENOLIEL, L. R. LYONS 4 AND W. H. PAHL.

I hope this helps. I planned to run this experiment years back but could not get a hold of methyl ethyl ketone :/. If you do this can you please report back what you find.

Attachment: Electrolytic Reduction of Methyl Ethyl Ketone.pdf (528kB)
This file has been downloaded 774 times


[Edited on 22-5-2015 by smaerd]

AvBaeyer - 22-5-2015 at 18:16

You might also consider a baker's yeast reduction. If it works, it will in all likelihood give a single enantiomer if that is important.

Plenty of information exists on this type of reduction if you do the search.

AvB

CuReUS - 22-5-2015 at 23:49

this thread will help you.many reducing agents for reducing carbonyl group to alcohol were discussed.take your pick
http://www.sciencemadness.org/talk/viewthread.php?tid=17051

vmelkon - 27-5-2015 at 09:28

Thanks guys.
As for smaerd's pdf document what is carbinol? I assumed they are talking about methanol while reading it but then I saw this line

"The boiling point of the pure carbinol is 99.5-100 C".

(((((http://www.thefreedictionary.com/carbinol
1. See methanol.
2. An alcohol derived from methanol.))))

It's suppose to be some magical mystery product?

DraconicAcid - 27-5-2015 at 09:33

Quote: Originally posted by vmelkon  
Thanks guys.
As for smaerd's pdf document what is carbinol? I assumed they are talking about methanol while reading it but then I saw this line

"The boiling point of the pure carbinol is 99.5-100 C".

(((((http://www.thefreedictionary.com/carbinol
1. See methanol.
2. An alcohol derived from methanol.))))

It's suppose to be some magical mystery product?


Carbinol is basically a synonym for alcohol. If you want to refer to 2-butanone as "methyl ethyl ketone", then it's consistent to refer to 2-butanol as "methyl ethyl carbinol" (i.e., a methanol with a methyl and an ethyl substituent), and that's "the carbinol" that you've made.