Diethylstilbestrol is also made in the following manner: 4-hydroxypropiophenone undergoes pinacone reduction using sodium amalgam, which gives the corresponding pinacone (28.1.34). Next, the resulting pinacone undergoes a pinacone rearrangement by a reaction with hydrochloric acid, forming ketone (28.1.35). The keto-group in this compound is reduced using sodium in isoamyl alcohol, which gives the corresponding carbinol (28.1.36). The resulting carbinol is treated with hydrochloric acid, which is simultaneously dehydrated and the rearranges into diethylstilbestrol (28.1.33) [45,46].
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