JMAPScience Posted January 8, 2014 Posted January 8, 2014 I have paradichlorobenzene and I want to make benzene. I have put the crystals in a solution hoping It would make 1,4 phenol. Will that happen? If not could I get a procedure for making a phenol from dichlorobenzene?
rktpro Posted February 21, 2014 Posted February 21, 2014 Why do you think that water would attack as nucleophile. The ring isn't deactivated for a nucleophillic substitution.
rktpro Posted February 23, 2014 Posted February 23, 2014 I wonder why the substance is crystalline? Try hydrogenation over Pd/C. It won't work either. If you go drastic you might loose the aromatic system.
John Cuthber Posted February 23, 2014 Posted February 23, 2014 I'd not even try to do that conversion. There are other materials from which you could make benzene much more easily. Also, messing about with dichlorobenzene and hot catalysts is a potential recipe for making PCBs On a related note, something like this http://www.researchgate.net/publication/229666203_The_hydrodechlorination_of_chloroaromatic_and_unsaturated_chloroaliphatic_compounds_using_a_nickel_boride_reagent might give a clue. The material is solid because of two factors, the aligned dipoles of the C Cl bonds and the van der Waals forces. The former must be significant, because the other two isomers are liquids.
Knumbnuts Posted February 23, 2014 Posted February 23, 2014 I wonder why the substance is crystalline? It won't work either. If you go drastic you might loose the aromatic system. Gentle hydrogenation over Pd/C removes halogen. Using a Rh cat e.g. Nishimura's cat hydrogenates the aromatic ring.
rktpro Posted February 23, 2014 Posted February 23, 2014 Gentle hydrogenation over Pd/C removes halogen. Using a Rh cat e.g. Nishimura's cat hydrogenates the aromatic ring. How would you make it gentle? With an inhibitor?
hypervalent_iodine Posted February 23, 2014 Posted February 23, 2014 If you didn't heat it or have it under pressure, it should be fairly straight forward to avoid reducing the phenyl ring.
rktpro Posted February 23, 2014 Posted February 23, 2014 (edited) It might be because of its high mass too. If you didn't heat it or have it under pressure, it should be fairly straight forward to avoid reducing the phenyl ring. I was thinking of using BaSO4 as an inhibator. Edited February 23, 2014 by rktpro
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