By Richard S. Monson
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Extra resources for Advanced Organic Synthesis. Methods and techniques
68B, 2091 (1935). 14. M. Yanagita and K. Yamakawa, /. Org. Chem. 21, 500 (1956). 15. G. F. H. Green and A. G. Long, /. Chem. , p. 2532 (1961). 16. E. A. Fehnel, S. Goodyear, and J. Berkowitz, /. Amer. Chem. Soc. 73, 4978 (1951). 17. E. L. Bennett and C. Niemann, /. Amer. Chem. Soc. 74, 5076 (1952). 18. D. S. Noyce, B. N. Bastian, P. T. S. Lau, R. S. Monson, and B. Weinstein, /. Org. Chem. 34, 1247 (1969). 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.
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once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods.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.
Trans-4-CHLOROCYCLOHEXANOL (77) -O OH To 10 g of cyclohexane-l,4-oxide is added 40 ml of 12 N hydrochloric acid solution. The solution is mixed thoroughly and allowed to stand at room temperature for 8 days. Water (50 ml) is added to the mixture, the phases are separated, the aqueous phase is extracted with 25 ml of ether, and the ether extract is combined with the organic phase. The ether solution is washed with bicarbonate solution and water and dried over anhydrous sodium sulfate. Ether and unreacted oxide are removed on a rotary evaporator, and the product is recrystallized from petroleum ether, mp 82-83° (yield, 8 g).
Advanced Organic Synthesis. Methods and techniques by Richard S. Monson