Sciencemadness Discussion Board

allylbenzene distillation issue

chemrox - 24-4-2009 at 08:57

After being quoted some really ridiculous prices for allylbenzene I decided to make it. I followed a published (H E Carter, J Biol Chem 108, 619 (1935) procedure using a Grignard reagent and allyl Br. Distilling the material after breaking up the complex with dilute acid I collected some residula material at 45*/aspirator vac and again with a new flask at 65-75* I ran an air bubbler and immediately got a visible vapor on top of the distillate that will not condense in the glassware. I changed from air to N2 with no change. ( Stirring would not prevent the foaming from overwhelming the still.) What might that be? (I ran a rotary evap on the stuff before distilling).

Second, why not make this from benzene and allyl-Br with AlCl3?

sparkgap - 24-4-2009 at 09:59

Quote: Originally posted by chemrox  
why not make this from benzene and allyl-Br with AlCl<sub>3</sub>?


I mentioned in passing in my thread alkylating benzenes with polyenes via Friedel-Crafts would most probably result in a "mess". That was because I found, among other things, this paper. Made me sad, too.

sparky (~_~)