I'm a beginner in organic chemistry and I wish to produce methyl 2,4,6-trimethylbenzenesulfonate.

My reactants are 2,4,6-trimethylbenzenesulfonyl chloride (solid crystals) and methanol (solvent as well as reactant). The product of this reaction should be methyl 2,4,6-trimethylbenzenesulfonate and HCl.

Now I've tried these many conditions: distilling the methanol, nitrogen inert atmosphere, slight heating about 40 °C, room temperature, closed system.

After trying these conditions and their combinations I'm not getting the product in the desired amount.

Kindly help me out and suggest a few tweaks and optimizations if possible. As far as my knowledge goes the problem seems to be with methoxy group.

This is the entire synthesis process, please check it out. I am stuck on step two of this synthesis.

Entire synthesis


closed as unclear what you're asking by orthocresol Aug 15 '17 at 6:32

Please clarify your specific problem or add additional details to highlight exactly what you need. As it's currently written, it’s hard to tell exactly what you're asking. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

  • $\begingroup$ Can you add structures or link to structures? Maybe I'm missing something, but the names of these compounds don't make sense. Trimethyltoluene sulfonate would be a tetramethylbenzene sulfonate, of which there are a couple isomers. $\endgroup$ – jerepierre Jan 13 '16 at 8:54
  • 1
    $\begingroup$ I guess, you want to prepare methyl 2,4,6-trimethylbenzene-1-sulfonate from 2,4,6-trimethylbenzene-1-sulfonyl chloride. Could you please check and edit your question? $\endgroup$ – Loong Jan 13 '16 at 12:32
  • $\begingroup$ @jerepierre and others, guys sorry for the delay. I have added the structures and the synthesis process please have a look. $\endgroup$ – AVyas Jan 14 '16 at 23:32
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    $\begingroup$ @AVyas I've changed the name of the compound to methyl 2,4,6-trimethylbenzenesulfonate, which is the product of reaction 1. I am still confused though because your edit says that you are having problems with step 2, which is the transfer of the methyl to a pyridine. Could you clarify which step you are having problems with and what exactly the problem is? "Not getting the product in the desired amount" could be anything. $\endgroup$ – jerepierre Jan 15 '16 at 0:58
  • $\begingroup$ I'm closing this as unclear because I cannot tell which step there is a problem in and what the problem actually is, cf @jerepierre's comment above. $\endgroup$ – orthocresol Aug 15 '17 at 6:33

Are you following a literature procedure? It looks like you should be able to find a reliable method that you can reproduce. Some general hints for optimisation:

  • Use a base to mop up the $\ce{HCl}$ that is produced. Either an organic base like pyridine (preferably) or triethylamine or you can use an inorganic base like $\ce{NaOH}$ or $\ce{Na2CO3}$ under Shotten-Bauman conditions i.e. as a biphasic aqueous-organic system
  • Increase the reactivity of the nucleophile. Methoxide is a much better nucleophile. You can use commercially available $\ce{MeONa}$ or you can create it by something like $\mathrm{^tBuOK/MeOH}$

EDIT: I am assuming OP tries to make methyl 2,4,6-trimethyl toluenesulfonate since he states that MeOH is a reagent.


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