ChemichaelRXN - 13-12-2020 at 06:59
Hello,
Has anyone ever performed a Grignard reaction where you are reacting two halogen groups with two moles of the ketone? Using the compound
1,4-dibromobutane and acetone or even MEK.
The compound Id produce would be 2,2,7,7-tetramethyloxepane, somewhat similar to 2,2,5,5-tetramethyltetrahydrofuran (TMTHF), naturally found in the
mycelium of Tuber borchii (truffles). I’d try to use H-Beta-zeolite for the cyclization of 2,7-dimethyloctane-2,7-diol.
I think it would be a fun couple step reaction to do, but I want to know what to expect in the Grignard. Think it would spontaneously combust?
Pumukli - 13-12-2020 at 08:06
Ask Henry Gilman! :-)
He studied Grignard reactions extensively and compiled a good article on them in "Organic Reactions" in the 1940-ies. He even mentioned the reactions
of alpha,omega-dihaloalkanes in that article... As far as I remember his verdict was this route was OK and went more or less according to theory.
So I encourage you to pursue this route, your target compound seems (smells?) gorgeous! :-)
ChemichaelRXN - 13-12-2020 at 09:43
Yea, it might just work. I recall hearing anything less than the 1,4-dibromobutane would just break apart. I will have to wait until the summer before
I can do this. I dont handle anything flammable with a low boiling point like THF or ether indoors in the fume hood and would do this outside. I have
the 1,4-dibromobutane and pretty much everything else luckily. Apparently that dihaloalkane is bad for the eyes, which makes me a little lazy about
handling it.
Yea, the odour must be reminiscent of the 2,2,5,5-tetramethylTHF. I would definitely document the product well if I achieve success with the final
cyclization.