So I've been reading TSII again, and I read the section on purifying safrole for the first time. The thing that
really caught my eye was the bit about using conc. H
2SO
4 to isolate an allylbenzene, which is then hydrolyzed to the alcohol on the
alpha carbon, which can be processed with a bisulfate to give the propenylbenzene as the final product. The example given was even for elemicin from elemi oil, and ended up with isoelemicin, which was what I was looking for anyway!
So is this true? Could it be? Please tell me this will work!
And another thing, I've read some discussions here about trying to get MDP2Pol via a markovnikov reaction using cold sulfuric, but it seems do want to do what Strike describes in TSII, and let the -OH stabilize on the
alpha carbon. So what? Couldn't the sassy oil be thrown in a pot with some ice cold conc. sulfuric, then the acid drawn off, and water thrown in, and it heated, and then left out for a day or two to make sure all of the -OH has migrated to the
alpha pos? Well, I guess it could be washed first, to get rid of all that sulfuric, which would be hell on the MD ring. But then it could be processed with a bisulfate to isosafrole, very quick and easy, and very pure! Is this feasable? Or does conc. sulfuric polymerize safrole, even at low temps? Should 70% be used?
It is seductive, way too seductive. -Eleusis