Alright so swim is interested in collecting the n-oxide in the basic solution that hot naptha won't extract so whats the best way to go about this? The idea so far is to extract the basic solution with xylene, wash that with vinegar acidified water. Make the aq solution basic with NaOH then extract with DCM and evaporate the DCM and scrape the oil around until it solidifies into a waxy yellow solid. However I'm sure there will be a degree of plant oils present (acacia bark). Any ideas how to separate plant oils and n-oxide short of doing a reduction with zinc?

After some searches another somewhat quicker idea would be to just extract with xylene then wash with vinegar and boil off that vinegar on a double boiler.

Your origional idea would work fine and there would be very little plant oils if you would be acidifying between non-polar extractions.

I've had significant yields doing a similar method, except using limonene instead of xylene. I then basified the n-oxides with Ca(OH)2 because it was faster than trying to get the acetate goo to solidify. I do hate evaping vinegar however. The stink is strong and lingering. Pewwww!

With Humility,
-idt