Lex
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Isophorone from acetone
Hi all
Has anyone explored the self-aldol condensation of acetone? I'm targeting isophorone (I want to explore it as a catalyst for decarboxylation of alpha
amino-acids via a Schiff base intermediate which can stabilise the carbanion intermediate through resonance, but that's by-the-by).
I can see a prep in Vogel for mesityl oxide (via single aldol followed by an iodine-assisted dehydration) but the reaction employs baryta, which is
not presently in my tool set. One can also find numerous patents online for isophorone from acetone, but all that I have seen employ either a
gas-phase reaction or liquid-phase at very considerable temperatures and pressures, none of which are consonant with my desire for self-preservation.
Acetone, NaOH, and KOH are all readily available and I am not overly concerned with yield - I just want some catalytic amounts of isophorone to play
with, so I was planning to experiment a bit with different methods and see if any isophorone is recoverable (e.g. (1) stir up a slurry of acetone with
KOH and (some sort of non-CaCl2) desiccant; or (2) just reflux up some KOH and acetone and see what happens).
But before embarking on this I thought I'd see whether anyone here has any experience or advice? I can't find any reported attempts elsewhere on the
forum so maybe this is a fool's endeavour.
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kmno4
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Christmas comes early this year - look at 3rd page of "Organic chemistry" section.
Or just UTFSE.
ps. I see now that TFSE works badly.
It makes a difference if you search "Isophorone" and "isophorone", subject/body also gives false results - at last something to do for bored
"administrator" creating 0-value posts on industrial scale 
[Edited on 11-12-2024 by kmno4]
Слава Україні !
Героям слава !
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chempyre235
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I remembered an SM thread which highlighted aldol condensations with acetone. There will be a myriad of compounds produced with this reaction: mesityl
oxide, phorone and isophorone will be among these.
Here's the link to the thread.
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
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Lex
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Registered: 4-2-2019
Location: New Zealand
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Quote: Originally posted by kmno4  |
ps. I see now that TFSE works badly.
It makes a difference if you search "Isophorone" and "isophorone", subject/body also gives false results - at last something to do for bored
"administrator" creating 0-value posts on industrial scale
[Edited on 11-12-2024 by kmno4] |
Aha! That must have been my issue as I'm seeing the hits now. Will explore. Thanks both for the responses
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