By Richard S. Monson
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Extra info for Advanced Organic Synthesis. Methods and techniques
7 Miscellaneous Elimination, Substitution, and Addition Reactions The following experimental procedures do not fall into any convenient categories, but all require reagents and techniques of general interest in organic synthesis. I. Methylenecyclohexane by Pyrolysis of an Amine Oxide The pyrolysis of amine oxides is a reliable synthesis of unrearranged olefins. Its importance in this regard, however, has largely been reduced by the development of the Wittig reaction (Chapter 11). Nevertheless, the present reaction still plays a role in the degredation of naturally occurring nitrogen-containing compounds, and it is included here as an example of the techniques employed.
1 g of 5% rhodium on alumina is hydrogenated at 50 psi in a Parr apparatus. Three equivalents of hydrogen are rapidly absorbed. The catalyst is removed by filtration through celite, III. HYDROGENATION OF /7-HYDROXYBENZOIC ACID 41 and the solvent is evaporated. The oily residue is dissolved in a minimum amount of petroleum ether, and crystallization is induced. The mixture of cis- and trans-cyclohexanediol has mp 98-100°. III. cis-4-Hydroxycyclohexanecarboxylic Acid from/i-Hydroxybenzoic Acid The rhodium catalyst previously discussed is employed in the hydrogenation of /7-hydroxybenzoic acid.
M. Downie, J. B. Holmes, and J. B. Lee, Chem. lnd. (London), p. 900 (1966). J. B. Lee and I. M. Downie, Tetrahedron 23, 359 (1967). A. W. Friederang and D. S. Tarbell, /. Org. Chem. 33, 3797 (1968). G. A. Wiley, R. L. Hershkowitz, B. M. Rein, and B. C. Chung, /. Amer. Chem. Soc. 86,964 (1964). D. Levy and R. Stevenson, J. Org. Chem. 30, 3469 (1965). J. P. Schaefer, J. G. Higgins, and P. K. Shenov, Org. Syn. 48, 51 (1968). REFERENCES 53 7. C. Djerassi, Chem. Rev. 43, 271 (1948); L. Horner and E.
Advanced Organic Synthesis. Methods and techniques by Richard S. Monson