Sciencemadness Discussion Board

Is there any replacement for Di Ethyl Ether?

FrankMartin - 13-4-2011 at 14:15

I was hoping some other ether such as t-Butyl Methyl Ether might function as a grignard solvent, and for most other purposes.

GreenD - 13-4-2011 at 15:18
Quote:

In spite of its hazards, ethyl ether seems to be the most generally satisfactory
solvent for preparing G r i g n a r d reagents. Higher boiling ethers, tetrahydrofuran, tert
i a r y amines, and hydrocarbons have been recommended but i n most cases its good
solvent power, low cost, high commercial purity, and ease of recovery make ethyl
ether the solvent of choice for G r i g n a r d reactions. The reaction is u s u a l l y carried out
under a pressure of about 20 pounds i n order to raise the b o i l i n g point of ether to a
temperature where jacket cooling is sufficient to prevent boiling. Higher temperatures,
however, often lead to lower yields, presumably through the W u r t z and disproportionat
i o n reactions.


Hope that answers your question... It would also depend on how reactive your substrates are...

starman - 13-4-2011 at 16:51

Do you have a particular reason to avoid it ? Hazards? Availability?

mr.crow - 13-4-2011 at 18:21

t-butyl methyl ether can substitute for ether as an organic solvent for extractions. So can DCM, toluene, ethyl acetate, etc. Depends on the solubility.

It can't be used for grignards. The t-butyl group blocks the ether that is needed to stabilize the Mg in the solution. THF, diglyme, butyl diglime, etc, all have ethers than can do this. they also form those evil peroxides