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
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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Update: June 2012