I was wondering about the ozonolysis of cyclohexane and further treatment with $\ce{H2O2}$. I understand that the product to this reaction is hexanedioic acid.

How could we substitute the $\ce{-H}$ on each carboxylic group to a methyl, as in the following structure:

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I am pretty sure it would be by adding two moles of methanol (Fischer esterification). Is this procedure correct?

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    $\begingroup$ I would try $\ce{NaOH}$ and then $\ce{MeI}$. And in one step but more dangerous you can prepare in a solution of $\ce{CH2N2}$. $\endgroup$ – ParaH2 Jan 17 '17 at 18:32
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    $\begingroup$ I think I would prefer sodium hydride to sodium hydroxide. Otherwise, agree with everything else. $\endgroup$ – Zhe Jan 17 '17 at 18:50
  • $\begingroup$ Oh, I see. But I thought Williamson synthesis was used for synthesising ethers from alcohols? $\endgroup$ – Bee Jan 17 '17 at 20:06

You have a couple of options.

  • Your acid-catalyzed Fisher esterification is one of them. The downside is that water, which is liberated in the reaction, has a higher boiling point than methanol. You can't just destill it off to drive the reaction to completion.

  • Zhe and Hexacoordinate-C mentioned diazomethane and methyl iodide which might work well. You might want to make sure that your DNA does not get methylated.

  • The Steglich esterification, using dicyclohexylcarbodiimide (DCC) and N,N'-dimethylaminopyridine (DMAP) might be an alternative to the Fisher esterifiction.

  • You might want to try something different, using dimethyl carbonate as a non-cancerogenic alkylation reagent. The procedure is described in Green Chemistry Letters and Reviews, 2013, 61, 89-93 and uses potassium carbonate as a base, dimethyl carbonate as a reagent (and solvent), and tetrabutylammonium chloride as a catalyst.


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