Boffis
International Hazard
Posts: 1867
Registered: 1-5-2011
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So called Maple Lactone
I saw a seller on Ebay selling something called Maple Lactone or 3-methyl-1,2-cyclopentadione. Since the latter compound is not a lactone I was
initially suspicious that this was BS. However, after a bit of research I discovered there are two compounds that are referred to as Maple lactone,
the compound mentioned above and a true lactone called Sotolone (the lactone of 2-keto-3-methyl-4-hydroxypentanoic acid) and it is the principle
flavouring in fenugreek seeds. Incidentally, I noticed that the 3-methylcyclopentadione is listed in the Sigma Aldrich catalog with "maple lactone" as
a synonym.
I was so curious I thought I would buy some and see what I got. The compound arrived, it is a slightly off white crystalline powder with an amazing
butterscotchy/ maple syrup like aroma. But apart from sniffing it what could a frustrated, locked-down, SM member do with it?
Well the first thing that occurred to me is that if it is truely a cyclic vicinal dione it should undergo the benzilic acid rearrangement and
therefore ring contraction. If so this would probably represent the simplest possible OTC route to a cyclobutane derivative:
From this cyclobutane derivative? Perhaps decarboxylate to methyl cyclobutanol? Or perhaps the OH will go first and give methylbutenoic acid?
Another possibility might be to convert it to a dioxime, which may react with nickel etc like dimethylglyoxime.
Any other ideas?
[Edited on 23-5-2020 by Boffis]
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Pumukli
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Good find, Boffis!
Try the ring contraction at first. It would be interesting in itself if worked.
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