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
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)|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||27 January 1975|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Tony Diaz|
|Deposited On:||15 Apr 2010 21:32|
|Last Modified:||26 Dec 2012 03:23|
- Final Version
See Usage Policy.
Repository Staff Only: item control page