Yesterday I first brominated propiophenon with Cu(II)Br in ethyl acetate, and then filter off the Cu(I)Br. I though that the lacrymatory effect wouldn't be felt when the brominated ketone was dissolved in a solvent, but boy was I wrong... My eyes hurt like hell, and I felt it in my troat and nose too. And it lingered on for hours also! Then I reacted the filtrate with pyrrolidine. At the end of the reflux I had a almost black solution (caused by using a rubber stopper to attach a condenser to the flask I think), so I did a sort of A/B.
First I acidified it to PH 3 with HCl. That formed two layers, but I added some "chemically pure gasoline" anyway (n-heptane?) and shaked. Then the water layer was separated and made basic. The slighly red oil layer was separeted. (I guess I should have extracted this but I didn't). I boiled this to remove any solvent. After that it was dissolved in isopropanol and I started dripping in sulfuric acid. Immidiately a white precipitate started forming (whoho! I thought..), and soon enough the whole solution was so white that you couldn't look through it. That's when I decided to filter it and continue dripping in more acid later, to prevent any over acidification. But the problem is that the solution is completely impossible to filter. It stuffs up my filter immidiately.
After the failed filtering attempt I tasted some of the powder that stuck to the filter, and it seemed to taste slightly salty at some parts, and bitter at others. It seems that my product it contaminated with something that is so finely powdered that it clogs the filter. A salt of pyrrolidine? NaSO4?
I tried to filter it through a bed of sand, like I read somewhere, but that didn't work.
What can I do so I can filter this mess? I'm not exactly experienced with any synthesis at all, so I've never had this happened to me before. It kills me to be so near, and still not there!
Btw, some time ago it was mentioned that NaBr and KBr acted sedating. Could the Cu(I)Br act in the same way perhaps? If I finaly get my product I could probably use it...