Hey guys! I've a lurked for some time around here and I've finally gotten around to making account, mainly because I just can't find and answer to
this question of mine. I know that ethers are used for grignard reactions, and this end I have synthesized some diethyl ether just recently. However,
I was kinda turned off by ether's ridiculously low bp and I decided to look for alternatives. The most promising candidate I found was 1,4-dioxane,
which has a bp of 101.1, and can be easily synthesized from ethylene glycol. However, I then found a number of links, including this one:
which claim that dioxane forms some kind of adduct with the gringard reagent. So my question is, can dioxane be used as a replacement for ether in a
generic grignard reaction?
[Edited on 4-4-2015 by regioselective13]
[Edited on 4-4-2015 by regioselective13]hyfalcon - 4-4-2015 at 06:25
You might want to tell us which reaction you are attempting.DraconicAcid - 4-4-2015 at 06:53
It's also much more toxic than THF or diethyl ether.
It does form an adduct with magnesium chloride, so you actually get dialkyl magnesium forming in solution (rather than alkylmagnesium chloride). The
reactions still work, though.
[Edited on 4-4-2015 by DraconicAcid]regioselective13 - 4-4-2015 at 09:09
DraconicAcid, I'm aware of dioxane's toxicity and I will be doing this outside and in small quantities. So, even though the dialkyl adduct is formed
instead of the alkyl salt this shouldn't have any effect on the amount of solvent I need to use, right?
