Sciencemadness Discussion Board

Alternative solvents to DMF

roadhouse123 - 3-6-2006 at 13:15

Long time lurker, first time poster:

I am planning on performing a wacker oxidation (PdCl2, Quinol...) however I do not have easy access to DMF. I think that I may be able to substitute another polar aprotic solvent like Acetonitrile, Ethyl Acetate, Acetone, or DMSO but would like to get some input before I try it. Any thoughts?

Thanks!

Sergei_Eisenstein - 3-6-2006 at 17:13

DMA, CH3CN, DMSO, NMP

Vitus_Verdegast - 5-6-2006 at 12:21

Quote:

wacker oxidation (PdCl2, Quinol...)


What do you mean with quinol ?

A Wacker oxidation using PdCl2, Cu(2+) and H2O as the oxygen donor performed under O2 pressure uses a polar aprotic solvent like DMF. I have not heard of DMSO having been used succesfully with this system, but long time ago it was reported that polar protic IPA and EtOH substituted DMF well.

A Wacker oxidation using PdCl2 and p-benzoquinone ("quinone") as the oxygen donor is performed in methanol under atmospheric pressure. Quinhydrone is said to substitute for p-benzoquinone.

[Edited on 5-6-2006 by Vitus_Verdegast]

IPN - 5-6-2006 at 12:46

I have a similar question. Can I use DMSO, NMP or acetonitrile instead of DMF when converting a substituted (for example with a few alkoxy groups) benzyl bromide into benzyl cyanide using NaCN? Would be a lot easier if one of those worked, as DMF is just too expensive.. :(

[Edited on 5.6.2006 by IPN]

Sandmeyer - 5-6-2006 at 14:01

Quote:
Originally posted by IPN
I have a similar question. Can I use DMSO, NMP or acetonitrile instead of DMF when converting a substituted (for example with a few alkoxy groups) benzyl bromide into benzyl cyanide using NaCN? Would be a lot easier if one of those worked, as DMF is just too expensive.. :(

[Edited on 5.6.2006 by IPN]


Of course, but are you sure that DMF is more expensive than DMSO and NMP? :P