Preparation of propylcyclohexanes with functions on the 4 and 3' positions Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/wp988n00m

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  • The preparation of 4-(3-hydroxypropyl) cyclohexanone and of 4-(3-hydroxypropyl) cyclohexene and a number of their derivatives as potential precursors of asymmetrically substituted bicyclo [3, 3, 1] nonanes is described. The ketone, 4-(3-hydroxypropyl) cyclohexanone, was prepared from p-allylanisole by three different routes. Common to each route was an initial hydroboration-oxidation followed by a Birch reduction to give a 4-(3-hydroxypropyl)-1-methoxy-1, 4-cyclohexadiene. Mild acid hydrolysis and catalytic reduction converted this to the desired product. The enol-ether was converted also to the related acetate, then hydrolyzed and reduced to give 4-(3-acetoxypropyl)- cyclohexanone. Finally methanolysis of the enol-ether gave the dimethyl ketal and a series of related ketals was prepared from that substance. Readily available 4-cyclohexenecarboxaldehyde was used to prepare 4-(3-hydroxypropyl) cyclohexene. This was accomplished via a normal chain elongation series employing a Grignard reaction with ethylene oxide as the crucial step. The tosylate of the unsaturated alcohol gave a mixture of unidentified acetates when solvolyzed. An attempt to prepare a comparison sample of 2-acetoxy-bicyclo [3, 3, 1] nonane from cyclohexanone enamine and acrolein was abandoned where only a low yield of 2-bicyclo [3, 3, 1] nonene was obtained on pyrolysis of the amine oxide of 2-pyrollidinobicyclo- [3, 3, 1] nonane.
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