Final Project Spring 2011: Part V

The fourth synthesis project started with the dehydration of cyclohexanol. We had performed the dehydration of 2-methylcyclohexanol during the Fall semester. The resulting cyclohexene was oxidized by hydrogen peroxide in the presence of a phase-transfer catalyst. This reaction was featured in a 2000 JCE article. There was some unreacted cyclohexanol with the cyclohexene but that did not seem to interfere with the oxidation step. We had done this experiment in during Spring 2008. Adipic acid can be characterized by IR and melting point. It does not exit the GC very well and the lack of chromophore makes it hard to detect by UV-vis methods. The resulting dicarboxylic acid was esterified with ethanol and boiling sulfuric acid. This last step was done in pretty low yield but the product was easily separated from the other substances by liquid-liquid extraction. 

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One Comment

  1. Posted June 25, 2011 at 11:00 am | Permalink

    Next step with my product–>NMR!

    I wondered if there was a way to tell in the final product if one or both carboxylivc acids in step 3 were replaced by an ester. It didnt’ seem like the analysis methods used could tell them apart (if both compounds existed).


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