KidCurry
Hazard to Self
Posts: 54
Registered: 12-3-2004
Location: Europe
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Why doesn't IPA work as a solvent for Henry reaction?
Was going to prepare nitrostyrene by base catalysed henry reaction (followed by acid dehydration of the alcohol) and had run out of methanol, but had
some isopropanol handy and didn't really think anything about it else than it should work.
What was strange here was that:
1) When the addition of KOH started, thesolution turned to green and something yellowish/orange fell out.
2) The temperature was more or less impossible to keep down.
I actually succeeded to get decent yields ONCE but two other attempts failed and yielded only some polymer funky oil or something. So, what's up
here. Am I missin the obvious? Does KOH/NaOH react with IPA? It just bugs me out not to know what happened, at first I thought it just was dirty
glassware and that something else interferred but it obviously was not the case.
Help me out! 
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flyingbanana
Harmless
Posts: 38
Registered: 1-3-2005
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i think IPA should work as long as the solubilities are kept in check some way or another, i've read some procedures that use it (not sure about
the yields though) so without further analysis i have no idea what happened
but on a side note, if you can't get IPA to work, you can just try using an excess of nitroalkane as solvent, it's been done
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