[Cokacola]

So I am trying to oxidize an alkene to a carboxylic acid. The compound is a large non-polar molecule (5 aromatic rings with a ketone, positively charge N, and 2 tertiary amines). I need to use sulfuric acid solution for the source of protons for the oxidation reaction. I need an organic solvent that will not react with the acid or potassium permanganate. DMSO, DMF, and Acetonitrile are no-go as I have already tried the test in which I dab some of the solvents mentioned and put potassium permanganate on it, all turned brown so I knew the solvents reacted with the potassium permanganate. Does anyone have any suggestions?

[mikeja]

Listing or giving a structure of the compound would help. Any CAS number or chemdraw or something you could provide? Also, why sulfuric acid/KMNO4 in the reaction? Do you want the oxidation to be under acidic condition, can you use another oxidant? You could also give more specifics on the reaction, what temp/concentrations etc you want to run it at. Basically list more info.

[TheUnassuming]

Have you done any reading as to how this is normally done?

There is a fair amount just a google search away and likewise on wikipedia.

In general, DMSO you will find is not a particularly good solvent for most reactions, and DMF only marginally better in harsh conditions.