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Question:
How could synthesize Dimestrol, an estrogenic hormone, from p-methoxypropriophenone as the only source of carbon? This is not a homework question, it is a question that my teacher gave us to prepare for the final examination. It is an example of what the questions will be like on the final, and I am very stuck and would like some help.



Replies:
It helps if you know the structure of Dimestrol. If your professor gives it to you, fine. Otherwise, you have to look it up. I did (I looked in the Merck Index). The structure of p-methoxypropriophenone is specified in its name, so you don't have to look it up. Seeing the two structures, several possible methods come to mind. The most direct would be to use a McMurry or Barton-Kellogg coupling. Somewhat less direct would be to reduce the propiophenone to the carbinol, convert to a bromide, and carry out a Wittig reaction between it and some unconverted propiophenone. Or, you could make a Grignard reagent from the bromide, add it to the ketone, and dehydrate the alcohol product - it will put the double bond in the proper place, because that puts the two aryl rings into conjugation. There are probably other ways you can envision, but those are the ones that occur immediately to me.

Richard E. Barrans Jr., Ph.D.



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