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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: smalhotr on October 09, 2015, 01:42:43 PM

Title: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: smalhotr on October 09, 2015, 01:42:43 PM

I was wondering if any one has had success in halogenating a hydroxyl group on an aromatic ring.

I am currently stuck at the step where I need to halogenate the two OH groups.

Any suggestions?
Link to Structure:https://pubchem.ncbi.nlm.nih.gov/compound/11469114#section=Top

Title: Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: kriggy on October 09, 2015, 03:45:25 PM

Well I think this isnt going to work. You might find some metal catalyzed reaction that might work but without that, you have highly deactivated system towards aromatic nucleophilic substitution.

Title: Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: smalhotr on October 09, 2015, 05:04:00 PM

Hmm, I see what you mean. What about halogenating the remaining unsubstituted carbons and somehow removing the OH? good ol' symmetry.

Title: Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: kriggy on October 10, 2015, 06:39:22 AM

Good thought but Im not realy sure if there are any methods to remove thy OH group from aromatic ring

Title: Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: orgopete on October 10, 2015, 09:17:04 AM

So, you want 2,3-dichloro-1,4-dimethylbenzene, http://www.chemsynthesis.com/base/chemical-structure-11581.html? You can buy it, http://www.molbase.com/en/name-2,3-dichloro-1,4-dimethylbenzene.html. Since it isn't novel, you could use that method to prepare your desired compound.

Title: Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
Post by: smalhotr on October 10, 2015, 12:21:55 PM

Thanks for all your responses.
Just in case you guys were curious, i figured out a way to halogenate the remaining unsubstituted carbons and remove the OH's using the following synthesis:

http://www.sciencedirect.com/science/article/pii/S004040200601862X

I'm going to give it a shot and see how that goes.