Advanced Organic Synthesis by Richard S. Monson

By Richard S. Monson

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Mild evacuation of the reaction vessel containing the catalyst prior to the introduction of hydrogen, and the flushing and evacuation of the vessel several times with hydrogen at low pressure will serve to prevent any difficulties. 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°.

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. 2, p. 228. Wiley/Interscience, New York, 1969. 10. A. Zurqiyah and C. E. Castro, Org. Syn. 49, 98 (1969) and references cited therein. Dissolving Metal Reductions Although once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods. Nevertheless, certain synthetic sequences that may require stereospecific or functionally selective reductions may best be executed by means of metals in solution.

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. 2, p. 228. Wiley/Interscience, New York, 1969. 10. A. Zurqiyah and C. E. Castro, Org. Syn. 49, 98 (1969) and references cited therein. Dissolving Metal Reductions Although once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods.

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