phendrol
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Registered: 13-6-2012
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Help! Acetone mistakenly used instead of IPA in al/hg reduction of b-nitrostyrene.
I wanted to reduce about 60 grams of b-nitrostyrene in a water/acetic acid/IPA mix. 200ml/600ml/200ml respectively. Acetone was sitting on my shelf in
the same PEHD bottle as IPA did. Of course they are labeled different but I didn't look at the label because I thought I'm holding the right one.
Well... I didn't  This is embarrassing but I noticed after I finished the
reaction, which proceeded just as it should. I got the post reaction mixture now which has a pink tint to it, and am wondering if I should discard it
or actually try to isolate the assumed product?
[Edited on 22-8-2014 by phendrol]
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FireLion3
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That doesn't sound good. Label your chemicals!!
You could try to isolate the reaction product.... but there is a strong possibility that when some of the amine was formed, an imine was then formed
with Acetone and then that was reduced. I'm not sure how much or if this reaction is likely to occur. If it doesn't occur, then some of the acetone
would have been reduced to IPA, and the worst thing that you would have had to contend with is the competitive reduction of Acetone vs your
b-nitrostyrene.
I wouldn't throw out the reaction, but I suggest evaporating off the acetone, adding IPA, and then redoing the reduction. You shouldn't even change
vessels, just heat and boil the acetone off, and add more aluminum. With the mercury still in solution the reaction will go further. Won't hurt to add
more GAA as well.
In the work up, you can work up as usual, but there may be some weird amine + acetone condensation product amines that will be hard to remove any
other way besides a distillation.
Maybe somebody else can speak up on the competition reaction of the acetone hydrogenation vs the b-nitrostyrene, but for that we would need to know
what your b-nitrostyrene is.
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