stygian - 6-12-2005 at 16:08
What would be a good solvent for the chlorination of benzoic acid with a catalytic amount of phosphorus (forming PCl5 in situ) that would not
interfere with chlorination? Would ether work?
BromicAcid - 6-12-2005 at 16:18
Don't use ether, chlorinated ethers are wicked carcinogens, try something fairly inert. I mean, what solvents do people normally preform
chlorinations in? Carbon tetrachloride springs to mind as it wouldn't be chlorinated further but the price and avilibility are major detractants of
its usefulness. There are probably some fluorocarbon mixtures out there that they sell specifically for that purpose, there's gotta be
something that I'm overlooking. As long as you keep it in the dark would free radical chlorination really be prominate, and as such couldn't
alkanes be used? Although the solubility of benzoic acid in such a medium might be crap.
joe_aldehyde - 8-12-2005 at 09:27
chloroform or DCM is a good solvent for that, i don't think they would be further chlorinated.
otherwise, if you use thionyl chloride for the chlorination you don't need any solvent, but a catalytic amount of DMF helps a great deal.
Marvin - 9-12-2005 at 00:40
I don't quite follow the original question. Arte you after a ring chlorination, or forming the acid chloride? How in this situation could the
phosphorous possibly be catalyctic?
stygian - 9-12-2005 at 08:42
Im after a COCl. I was going to say it worked by 2P + 3Cl2 = 2PCl5 which would be regenerated with more Cl2 but I now realize its going to form
POCl3. Hm.