204 REDUCTION WITH ALUMINUM ALKOXIDES PROCEDURE V * (FOR KETONES RESISTANT TO REDUCTION) Reduction of 4-Keto-l,2,3,4-tetrahydrochrysene (XXII) in Toluene. A solution of 8.2 g. (0.040 mole) of purified aluminum isopropoxide and 2.75 g. (0.011 mole) of 4-keto-l,2,3,4-tetrahydrochrysene in 25 cc. of dry toluene is refluxed for four hours, in an oil bath. After the solution has cooled slightly, 25 cc. of dry isopropyl alcohol is added to facilitate removal of acetone, the water is removed from the reflux condenser, and a water condenser set for downward distillation is attached to the top" by means of a short bent tube (a Hahn partial condenser with a 1-cm. layer of isobutyl alcohol in the inner condensing tube may be used). The mixture is heated at such a rate that slow distillation occurs (2 to 5 drops per minute^ the volume of solution should be maintained by further addition of solvent as needed). When the test for acetone is completely negative,! the toluene solution is cooled and the aluminum salt is de-
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