Would 100% isopropanol react with 1-bromo-3-chloro-5,5-dimethyl hydantion to give bromo/chloro-acetone? I have done an experiment with these things
and found that the lacrimaing properties of the resulting solution were consistent with each other. Would sodium acetate act as a catalyst in this
situation?guy - 26-9-2007 at 14:33
YesSauron - 26-9-2007 at 23:46
Well, I'm a little confounded by the disconnection between the thread title (2-propanol to acetone via oxidation) on the one hand, and the
halogenation question on the other.
KMnO4 will chew the alcohol to acetone, leaving you with a MnO2 mess to clean up. But that is preferable to having to deal with Cr(VI) which is the
unpalatable alternative.
Chloroacetone or bromoacetone are nasty lachrimators and quite toxic as lachrimators go, which is why they are no longer used for that purpose (riot
control). My advice would be, don't make them. Reconsider whatever your synthetic scheme might be and find an alternative route.sparkgap - 27-9-2007 at 00:16
I think he meant that he only wanted to confirm if his halogenating agent of choice will convert 2-propanol into nasty haloacetones. I'm not sure if acetate is only here as an acid catalyst or something else...
sparky (~_~)Sauron - 27-9-2007 at 01:14
If he wants to oxidize the -OH to carbonyl with a halogen source the one to use is TCCA whi will make acetone and not chloroacetone.chemrox - 27-9-2007 at 07:45
Maybe he wants chloroacetone for the Friedel-Krafts. He might need the money. Oh hell I better go to work!Antwain - 27-9-2007 at 10:06
Quote:
Originally posted by Sauron
KMnO4 will chew the alcohol to acetone, leaving you with a MnO2 mess to clean up. But that is preferable to having to deal with Cr(VI) which is the
unpalatable alternative.
Really? Even aside from availability, I would prefer to use the Cr(VI) with acid then distill the acetone out. Cr(III) is ok, and thats all you will
have left. With KMnO4 (I would again want to use acid, no sense in wasting your oxidising agent) Alternative reactions can occur, such as the fun and
excitement of turning the whole thing into CO2.
Then again you always have the enol oxidation, but thats not so bad at low temps. I have recently used KMnO4 solution in acetone for the fun and
excitement of making arsine oxides.
I'm not sure if acetate is only here as an acid catalyst or something else...