Sciencemadness Discussion Board

Isophorone from acetone

Lex - 11-12-2024 at 01:45

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.

kmno4 - 11-12-2024 at 04:20


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 :D

[Edited on 11-12-2024 by kmno4]

chempyre235 - 11-12-2024 at 07:49

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...

Lex - 11-12-2024 at 16:01

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 :D

[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