Sciencemadness Discussion Board

So called Maple Lactone

Boffis - 22-5-2020 at 14:05

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:


Maple  lactone.gif - 2kB

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]

Pumukli - 25-5-2020 at 02:54

Good find, Boffis!

Try the ring contraction at first. It would be interesting in itself if worked.