Optimum conditions for the lithium-liquid ammonia reduction of 4-t-butylcyclohexyl methanesulfonate(I) to t-butylcyclohexane(II) and traps-4-t-butylcyclohexanol(III) were determined. The mesylate I eater was synthesized from alcohol III which was prepared by the lithium aluminum hydridealuminum chloride reduction of commercial 4-t-butyloyclohexanone.The parameters of the lithium-liquid ammonia medium studied were: lithium concentration, proton source, reduction temperature, cosolvent, and reduction time. These parameters were examined in relation to their effect on the lithium-liquid ammonia medium to convert mesylate I to hydrocarbon II and alcohol III. The experimental results for these parameters demonstrated the optimum conditions for the production of hydrocarbon II to be the following: lithium concentration, 0.17 M; added acid, ethanol; reduction temperature, -3300; and cosolvent, ethyl ether. A reduction time of one hour is sufficient when these optimum conditions for the lithium-liquid ammonia medium are satisfied.Vapor phase chromatography and nuclear magnetic resonance spectroscopy were determined to be reliable techniques for the quantitative analysis of the reduction products. The nuclear magnetic resonance spectra of mesylate I and alcohol III were compared.
| Identifer | oai:union.ndltd.org:BSU/oai:cardinalscholar.bsu.edu:handle/180573 |
| Date | January 1972 |
| Creators | Renner, Christopher L. |
| Contributors | Wiseman, Park A. |
| Source Sets | Ball State University |
| Detected Language | English |
| Format | v, 52 leaves : ill. ; 28 cm. |
| Source | Virtual Press |
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