this may well be a fools errand and a waste of apiole, and i know some bees will be skeptical, but humour me. k?
ideally this might be manifest in a basic demethylation as acidic conditions seem to promote cylisation of a furan ring with the 2MeO. Yet dillapiole survives a buffered performic in good yeilds, so maybe just a mild de-methylation is called for.
what it would be nice to be able to do is go from
2,3-diMeO,4,5MDallybenzene
to
2,3-diHO,4,5MDallybenzene
to
2,3,4,5-diMDallybenzene (one of the 3 fabled bis-methylenedioxy paths to valhalla)
i like the idea of demethylating w AlCl3, but that 210C reflux afterwards is going to hurt. the reflux w/ 48%HBr RXN is one i am very leary of, and would save it as last ditch.
bees have any thoughts on how this might be successfully accomplished? last thing, any idea as to what properties might be expected of 2,3-diHO,4,5MDallybenzene. muchos gratias bees.
7.10.01