By Richard S. Monson
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Extra resources for Advanced Organic Synthesis, Methods and Techniques
4. A. C. Cope and E. Ciganek, Org. Syn. Collective Vol. 4, 339 (1963). 5. E. L. EHeI, Rec. Chem. Progr. 22, 129 (1961). 6. E. L. Eliel, R. J. L. Martin, and D. Nasipuri, Org. Syn. 47, 16 (1967). 7. R. A. Daignault and E. L. Eliel, Org. Syn. 47, 37 (1967). 8. Y. M. Y. Haddad, H. B. Henbest, J. Husbands, and T. R. B. Mitchell, Proc. Chem. Soc. London, p. 361 (1964). 9. E. L. Eliel, T. W. Doyle, R. O. Hutchins, and E. C. Gilbert, cited in M. Fieser and L. Fieser, "Reagents for Organic Synthesis," Vol.
A. 3-BROMOCYCLOHEXENE (8) NBS - * I Il + A 250-ml round-bottom flask is fitted with a condenser (drying tube), a magnetic stirrer, and a heating mantle. 1 g of benzoyl peroxide, and 50 ml of dry carbon tetrachloride. The flask is flushed with nitrogen and then refluxed for 40 minutes with IV. a-BROMINATION OF KETONES AND DEHYDROBROMINATION 49 stirring. The succinimide is removed by suction filtration and washed twice with 10-ml portions of carbon tetrachloride. The combined filtrate and washings are fractionally distilled at atmospheric pressure to remove the carbon tetrachloride and excess olefin (steam bath).
A. 1 g of 5 % rhodium on alumina for 16-18 hours at 50 psi initial pressure in a Parr apparatus. The reduction stops after the absorption of 1 equivalent of hydrogen. The catalyst is removed by filtration through celite, and the aqueous solution is carefully acidified with concentrated hydrochloric acid at 0°. The crude product is collected by filtration, dried in air, and recrystallized from benzene to give 1,3-cyclohexanedione, mp 105-107°. B. 1 g of 5% rhodium on alumina is hydrogenated at 50 psi in a Parr apparatus.
Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson