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Wolff-Kishner reduction is described in most introductory organic textbooks. However, the reaction is rarely included in undergraduate organic laboratory textbooks. Wolff-Kishner reduction of carbonyl groups is usually conducted with hydrazine hydrate in the presence of a strong base at elevated temperatures (about 200 (deg)C) for hours. Soriano reported a simple Wolff-Kishner reduction of isatin under mild condition (1). However, this method still required a 3- to 4-h laboratory period and the base, sodium ethoxide, had to be freshly prepared-which presents a potential danger for inexperienced chemists. Our undergraduate organic laboratory is scheduled for 2 h and 50 min, which includes 10 min of lab quiz and about 30 min of lab lecture. Therefore, the traditional Wolff-Kishner reaction cannot be carried out in our student laboratory or in most of the undergraduate organic laboratories in the U.S.A.
There have been reports (2-4) of significant decreases in reaction time for organic reactions carried out in...