The synthesis and solvolytic investigations of 2-hexanone-5-(p-N-methylpyridinium) ether and n-hexyl-p-carboxybenzenesulfonate

Citation

Bogan, Gary W. (1975) The synthesis and solvolytic investigations of 2-hexanone-5-(p-N-methylpyridinium) ether and n-hexyl-p-carboxybenzenesulfonate. Master's thesis, California Institute of Technology. doi:10.7907/SMH3-TM92. https://resolver.caltech.edu/CaltechTHESIS:03292010-092444069

Abstract

The synthesis and purification of 2-hexanone-5-(p-N-methylpyridinium) ether was accomplished. The reaction of this compound with aqueous NaOH failed to produce the desired products, cis- and trans-2-methylcyclopropylmethyl ketone. It appears that the desired anionic ring closure of the starting material did not take place, but instead, a simple displacement reaction occurred to produce 5- hydroxyhexan-2-one. In a second project, the synthesis of n-hexyl-p-carboxybenzene-sulfonate was attempted by two different routes. The first route involved esterification of p-carboxybenzenesulfonyl chloride and n-hexanol to form the desired sulfonate. This method proved unsuccessful, and was abandoned. The second route involved oxidation of n-hexyl-p-toluenesulfonate to the carboxy compound. This method was successful, producing n-hexyl-p-carboxybenzenesulfonate in about 7% yield. This molecule was found to have an approximate half-life of 14 hours when reacted with 1 N aqueous NaOD at room temperature.

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