chemrox
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diol to oxo conversion
I have a large quantity of 1,1 cyclopentane diol and I want to make some of it into cyclopentanone. I've looked everywhere I can think of for this
conversion with no luck. I tried a standard oxidation with KMnO4 and ended up with a purple mess that smelled like old gym socks. A pointer as to
where I might find the information would be appreciated. Thanks, CRX
"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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smuv
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1,1-cyclopentanediol...so the hydrate of cyclophentanone? typo?
Late edit: cyclopentanone not cyclophentanone (whatever that is)
[Edited on 8-20-2011 by smuv]
"Titanium tetrachloride…You sly temptress." --Walter Bishop
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ThatchemistKid
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This could be a shot in the dark but.. if you subjected it to dehydration conditions you could make a double bond between carbons one and two or one
and five (doesnt matter) enol keto tautomerization leads to cyclopentanone. I think I similar method is used to make acetyl aldehyde from ethylene
glycol under certain conditions.. granted though the hydroxyl groups are on different carbons in that case.
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ThatchemistKid
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actually wait..yes the hydrate of cyclopentaone did you mean 1,2 cyclopentane diol, that is what I thought your post said when I first read it? ..the
above mentioned method could still work in that case.
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not_important
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If it is the 1,1 diol then it's a hydrate. Dump into tolune and azetrope off the water.
If it's the 1,2 diol then the acid catalysed pinacol-typr rearrangement (with hydrogen migrating) will give the ketone.
Oxidation would give the diketone and/or ring opening to dicarboxilic acids and so on.
http://jjc.yu.edu.jo/Issues/Vol4No3PDF/05galley%20proof%20of...
http://en.wikipedia.org/wiki/Pinacol_rearrangement
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chemrox
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thanks-it is the 1,1 I'll try the azeotrope.. it wouldn't be bad to have it in toluene anyway
"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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