Suggestions for reaction conditions to prepare methyl 2,4,6-trimethylbenzenesulfonate [closed]








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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](https://i.stack.imgur.com/HyqjS.png)](https://i.stack.imgur.com/HyqjS.png)




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](http://www.organic-chemistry.org/namedreactions/schotten-baumann-reaction.shtm) 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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