Sciencemadness Discussion Board

MethylSulfonylMethane reduction with Zinc to DMSO

reactofurnace - 25-7-2015 at 03:42

will did the reduction of MSM and DMSO work.
C2H6O2S + Zn ----> (CH3)2SO + ZnO
What temperture do you recommend?
any suggestions?:)

Thanks

[Edited on 25-7-2015 by reactofurnace]

MeshPL - 25-7-2015 at 04:43

I'm not an expert regarding organic chemistry. Title of your topic is wrong: DiMethyl SulfOxide is DMSO. MethylSulfonylMethane is MSM.

So, if I were you and had plenty of reagents, time and no other information, I would try reduction with zinc, maybe magnesium or aluminium. Assuming the reaction described in your post is corrrect (may not be) a good aparatus would be a flask with MSM and zinc heated up to 190C connected to a condenser and coollector (DMSO boils at 189C, lower than MSM). Alternatively set up a reflux for a longer time and after a few hours try distilling DMSO out. Alternatively you could try adding an acid or a base to a mixture of MSM and Zn or Al (or just acid in case of Fe or Mg)-there are reductions that work that way, although they are not very efficient. I would not expect such reactions to proceed easily in room temperature not to mention the fact that MSM is solid in room temperature. For such reduction to work somekind of solvent may be required.

Wikipedia mentions LiALH4 to reduce sulfonyls to alkanes, not sure how though.

I would not expect succes though.

What I remember is, that oxidation of organic sulphides to sulphoxides is easier than sulfoxides to sulfonyls. What that means is, probably reduction of sulfones to sulfoxides is easier than sulfoxides to sulphides. But watch out for eventual DMS formation.

You'd better wait for someone more experienced to respond (and inform you that MSM reduction is not possible). Unless, nobody does.

Also, isn't MSM harder to get than DMSO (a common solvent)?

[Edited on 26-7-2015 by MeshPL]

reactofurnace - 25-7-2015 at 13:51

thanks the dms is easily separated by distillation. ill wait for some other suggestions though .
Quote:

What I remember is, that oxidation of organic sulphides to sulphoxides is easier than sulfoxides to sulfonyls. What that means is, probably reduction of sulfones to sulfoxides is easier than sulfoxides to sulphides. But watch out for eventual DMS formation.