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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. http://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.

Item Type:Thesis (Master's thesis)
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Bergman, Robert G.
Thesis Committee:
  • Unknown, Unknown
Defense Date:27 January 1975
Record Number:CaltechTHESIS:03292010-092444069
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:03292010-092444069
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:5644
Collection:CaltechTHESIS
Deposited By: Tony Diaz
Deposited On:15 Apr 2010 21:32
Last Modified:26 Dec 2012 03:23

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