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Additional resources for Advanced Organic Synthesis, Methods and Techniques
The reaction mixture is now stirred for an additional 20 minutes, and water (10 ml) is carefully added to destroy the slight excess of borohydride. When no further hydrogen is evolved, the solution is made alkaline by the addition of 15 ml of dilute sodium hydroxide solution, followed by 15 ml of 30% hydrogen peroxide solution added in 2-3 ml portions. The reaction mixture is now poured into a separatory funnel with 50 ml of ice water, and the cyclohexanol is removed by two ether extractions. The ether extracts are dried with anhydrous sodium sulfate, and the dried solution is distilled.
Angibeaud, M. Larcheveque, H. Normant, and B. Tchoubar, Bull. Soc. Chim. , p. 595 (1968). 8. E. E. van Tamelen, M. Shamma, A. W. Burgstahler, J. Wolinsky, R. Tamm, and P. E. Aldrich, /. Amer. Chem. Soc. 91, 7315 (1969). 9. W. Huckel and W. Kraus, Chem. Ber. 92, 1158 (1959). Hydroboration A remarkable variation of the hydride reduction is the addition to double bonds of diborane (B2H6) (7). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent.
C. trans-4-BROMOCYCLOHEXANOL (18) HBr /\^ ^^OH " Br, To 10 g of cyclohexane-l,4-oxide is added 48% aqueous hydrobromic acid (60 g). The phases are mixed thoroughly and allowed to stand at room temperature until the solution separates into two layers (usually 5 days). The mixture is saturated with sodium chloride and extracted twice with 25-ml portions of ether. The ether layer is washed with an equal volume of saturated sodium bicarbonate solution, then with the same amount of water. Finally, the ether solution is dried over anhydrous sodium sulfate, the ether is evaporated, and the residue is allowed to cool, whereupon crystallization should follow.