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Author: Subject: Oppennauer oxidation
GrayGhost
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[*] posted on 22-5-2015 at 09:22
Oppennauer oxidation


Viewed the thread aluminium isoproxide for Oppenauer oxidation, my question is.

Phenyl 2 propanol + acetone= P2P + 2 propanol ? is posible?

Note: Is chemical interest dont confuse with other things.Thanks.
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GrayGhost
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[*] posted on 23-5-2015 at 08:48


Well, I find the answer in The Hive.Thaks
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zed
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[*] posted on 24-5-2015 at 15:54


Well, it isn't the usual way. Seems I've seen a similar procedure, somewhere. An equilibrium exists, but it is hard to take advantage of it.

The reductions, via isopropylalcohol, are usually driven to completion by distilling off acetone as formed. You propose to use the opposite approach. Unfortunately, isopropyl alcohol is a higher boiler than acetone, so you are kinda swimming against the current. Acetone leaves the reaction medium more rapidly than isopropyl alcohol, so it is had to get it to stick around long enough to do its job.
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[*] posted on 24-5-2015 at 16:18


Quote: Originally posted by zed  
Well, it isn't the usual way. Seems I've seen a similar procedure, somewhere. An equilibrium exists, but it is hard to take advantage of it.

The reductions, via isopropylalcohol, are usually driven to completion by distilling off acetone as formed. You propose to use the opposite approach. Unfortunately, isopropyl alcohol is a higher boiler than acetone, so you are kinda swimming against the current. Acetone leaves the reaction medium more rapidly than isopropyl alcohol, so it is had to get it to stick around long enough to do its job.


Yes , it is difficult.As i read. Thank you.
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CuReUS
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[*] posted on 24-5-2015 at 22:21


honestly I don't understand why everyone is so crazy about doing oppenauer when there are so many easier and high yielding ways.oppenauer is a selective reaction to for the oxidation of sensitive alcohols such as conjugated alcohols ,or alcohols having other oxidisable groups,like amine.it is not a reaction that should be applied for all oxidations
the stevens oxidation is a much better,high yielding(>90%) and extremely cheap wasy to get ketones from alcohols
http://www.sciencemadness.org/talk/viewthread.php?tid=61390#...
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byko3y
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[*] posted on 24-5-2015 at 23:26


Chapman-Stevens (hypochlorite) oxidation doesn't work well for P2P, because it is a methyl ketone, so haloform will be a side reaction on high ph, and mono halogenation of ketone will be a side reaction on low ph.
H2O2 + PTC works well for water insoluble compounds, but Pyridine-chloroformate is easier.
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CuReUS
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[*] posted on 25-5-2015 at 01:37


Quote: Originally posted by byko3y  
Chapman-Stevens (hypochlorite) oxidation doesn't work well for P2P, because it is a methyl ketone, so haloform will be a side reaction on high ph, and mono halogenation of ketone will be a side reaction on low ph.

that was the same thing I had said in the thienyl acetone thread,but sadly we both are wrong.there won't be haloform as the medium is acidic.I suggest you read the paper.
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H2O2 + PTC works well for water insoluble compounds,

It would be very good if you could tell ways to find OTC PTC.
Quote:
but Pyridine-chloroformate is easier.

it would be,if pyridine was easy to get.also pyridine is not cheap last time I checked,so don't suggest buying it.(Its also watched so I wouldn't think of buying it either.)

[Edited on 25-5-2015 by CuReUS]
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Chemosynthesis
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[*] posted on 25-5-2015 at 02:02


Quote: Originally posted by CuReUS  

Quote:
H2O2 + PTC works well for water insoluble compounds,

It would be very good if you could tell ways to find OTC PTC.

Plenty of extremely common ones out there in sanitation.
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