Palladium
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DMF substitute in Wacker oxidation?
This is supposed to be performed in an aprotic solvent that is polar. Dimethylformamide is the preferred solvent in this case. I'm thinking of what
might be the substitute for DMF.
DMSO is also an aprotic solvent. Would this work?
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Hexagon
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What alkene are you working on? Sure plain methanol will not work?
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madscientist
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It should work. Even protic solvents such as t-BuOH have been used. But I would read a review paper on the Wacker oxidation to be sure, rather than
risking (valuable?) reagents.
I weep at the sight of flaming acetic anhydride.
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Palladium
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Ethene to acetaldehyde, to start with.
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Palladium
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Quote: Originally posted by madscientist  | | It should work. Even protic solvents such as t-BuOH have been used. But I would read a review paper on the Wacker oxidation to be sure, rather than
risking (valuable?) reagents. |
I haven't found any other solvent but DMF yet in reports. DMF is not allowed to use in Europe anymore, since its poisonous.
DMSO is in my opinion the closest, with even higher BP.
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madscientist
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Are you sure about this? A google search revealed that dimethylfumurate has been banned by the EU, but nothing about dimethylformamide.
I weep at the sight of flaming acetic anhydride.
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mr.crow
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Really? They won't allow a common laboratory solvent
N-Methyl Pyrrolidone may be a substitute. Polar aprotic solvent, an amide and nearly harmless
Double, double toil and trouble; Fire burn, and caldron bubble
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antibody
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What kind of wacker are you planning?
using benzoquinone as the O2 source will run fine using methanol as your solvent
there was a lot of discussion about this a few years back and people running the straight O2 wacker had mixed results with methanol, many had zero
success with it
there was some speculation that dmso would work but I never saw a success story with it posted anywhere
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Palladium
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| Quote: Originally posted by madscientist | | Are you sure about this? A google search revealed that dimethylfumurate has been banned by the EU, but nothing about dimethylformamide.
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Yes, quite sure. "EU forbids dangerous solvent, dimethylformamide (2009).
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