Advanced Organic Synthesis by Richard S. Monson

By Richard S. Monson

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IV. 5 ml of concentrated hydrochloric acid is added 15 ml of trimethylphosphite. 05 mole) of 4-t-butylcyclohexanone in 160 ml of isopropanol in a 500-ml flask equipped with a reflux condenser. The solution is refluxed for 48 hours, then cooled, and the isopropanol is removed on a rotary evaporator. The residue is diluted with 65 ml of water and extracted four times with 40-ml portions of ether. The extracts are dried with anhydrous magnesium sulfate, filtered, and the ether is removed on the rotary evaporator.

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once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods.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. The Birch reduction, or its modifications (I)9 employs a solution of an alkali metal in liquid ammonia or an aliphatic amine and is still widely used in connection with the reduction of aromatic or conjugated systems.

The alumina is allowed to stand with occasional swirling for 30 minutes. To the flask is added 20 g of 1,4-cyclohexanediol (Chapter 5, Section II). A short Vigreux column is placed over the flask, which is then arranged for distillation. The mixture is heated at 240° with a sand bath or mantle, whereupon distillation commences (caution, bumping). The distillation is continued until the alumina is dry (5-8 hours). The distillate, which consists of two layers, is added to 75 ml 52 6. THE INTRODUCTION OF HALOGEN of pentane, and the aqueous layer is drawn off.

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