Is it possible to reduce raspberry ketone (4-(4-Hydroxyphenyl)butan-2-one) to ethyl methyl ketone? How would I do this in practice?
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3$\begingroup$ In practice you should simply buy butanone ;) $\endgroup$– MithoronCommented Apr 11, 2015 at 14:00
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$\begingroup$ Well, that should probably be the right answer. I just need a small amount though, I don't want to buy a whole litre, and I have 4-(4-Hydroxyphenyl)butan-2-one already. I thought I would ask to see how difficult it is, since it may be easy (I don't know a lot of chemistry) $\endgroup$– RockyCommented Apr 11, 2015 at 14:40
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1 Answer
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There are a number of ways to accomplish your goal, but they all involve several synthetic steps. As mentioned in the comments, it's always easier to buy a compound then run a reaction, but if you had a small amount of some exotic derivative, you could convert it to methyl ethyl ketone.
One possible route would be to convert the raspberry ketone to an ester using the Baeyer-Villager reaction. In this reaction the secondary (ethyl) branch migrates in preference to the primary (methyl) side. The resulting ester can then be converted to the desired ketone by any number of methods such as the Weinreb route.
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$\begingroup$ Wow epic. Chemistry blows my mind. So after the baeyer-villager reaction, which particular ester would be left? $\endgroup$– RockyCommented Apr 11, 2015 at 16:00
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$\begingroup$ After the Baeyer-Villiger you would have the ester pictured in the top-right corner of my drawing. It is just your starting Raspberry ketone with an oxygen inserted between the carbonyl and the p-hydroxyphenethyl group. If this answer was helpful please consider accepting and\or up-voting it, thanks. $\endgroup$– ronCommented Apr 11, 2015 at 16:06
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$\begingroup$ Also, if I did a Catalytic Baeyer-Villiger oxidation using hydrogen peroxide, and hydrochloric acid as a catalyst, would that give me Methyl ethyl ketone peroxide, an explosive? $\endgroup$– RockyCommented Apr 11, 2015 at 16:07
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$\begingroup$ No, peroxides are thought to be intermediates in the reaction, but they are not isolated. Rather the presumed peroxide intermediate rearranges further during the reaction to yield the final product. $\endgroup$– ronCommented Apr 11, 2015 at 16:13