Sciencemadness Discussion Board

Dichloro m-xylenol reactivity

wg48temp9 - 31-10-2019 at 02:12

Are the Cls in DCMX more reactive than the ones on p dichlorobenzene?

I am considering buying some DCMX and I am hoping that as it a phenol the Cls will be reasonably reactive meaning more reactive than PDB.



Pumukli - 31-10-2019 at 07:50

More reactive in which reaction? :)

If you are thinking about nucleophile substitution then the answer is no. No because it'd require strong electron withdrawing groups to "activate" the chlorines towards nucleophilic susbstitution. o-and p- substituents relative to the chlorine are required for such an effect, m-substituents have no effect.
Moreover those methyl-groups may flank the chlorines nicely, further decreasing their reactivity.

You read my theory.
Now let's allow others to chime in! :)

wg48temp9 - 31-10-2019 at 09:39

Quote: Originally posted by Pumukli  
More reactive in which reaction? :)

If you are thinking about nucleophile substitution then the answer is no. No because it'd require strong electron withdrawing groups to "activate" the chlorines towards nucleophilic susbstitution. o-and p- substituents relative to the chlorine are required for such an effect, m-substituents have no effect.
Moreover those methyl-groups may flank the chlorines nicely, further decreasing their reactivity.

You read my theory.
Now let's allow others to chime in! :)



Hopefully its an easy route to various xylenol derivatives used in the synthesis of various triarylmethane dyes. Such as m-xylenol, substituting the Cl p to the the OH with various amines and perhaps the Cl o to the OH with SO3H.

At about 14pounds for 500ml including delivery its cheap.

[Edited on 10/31/2019 by wg48temp9]

Pumukli - 1-11-2019 at 02:35

Your planned reactions have no chance to work on this substrate.
You would need either nitro or cyano or a few other, similarly strong electron withdrawing groups to make the chlorines reactive enough.
The methyl groups are not electron withdrawing, they are electron releasing, OH too.

Check the requirements of aromatic nucleophile substitution in the literature!