roadhouse123
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Alternative solvents to DMF
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!
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Sergei_Eisenstein
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DMA, CH3CN, DMSO, NMP
damnant quod non intelligunt
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Vitus_Verdegast
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| 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]
Sic transit gloria mundi
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IPN
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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]
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Sandmeyer
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| 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? 
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