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Topic: Trying a new synthesis-need the correct intermediate  (Read 1831 times)

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Offline zsinger

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Trying a new synthesis-need the correct intermediate
« on: November 14, 2013, 09:38:46 PM »
All,
converting 1-methyl-cyclohexanone into 1,1,-dimethyl-cyclohexanone.  I know that the enolate formed with the addition of base to 1-methyl-cyclohexanone favors the kinetic enolate (I.E. snagging a labile hydrogen on the less substituted side of the ketone).  So my question lies here:  What is a good way to avoid heating the mixture so I don't get any competing elimination reactions, while still getting the thermodynamic enolate?  Any help appreciated, as I have never tried this one.  The LDA at -78C is easy to make the other substituted ketone, however I've never tried to purposefully make the other one.  Thanks.
              -Zack
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Offline Babcock_Hall

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Re: Trying a new synthesis-need the correct intermediate
« Reply #1 on: November 15, 2013, 09:39:57 AM »
Do you mean 2-methylcyclohexanone?

Offline zsinger

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Re: Trying a new synthesis-need the correct intermediate
« Reply #2 on: November 15, 2013, 04:28:41 PM »
Yes……damn IUPAC…..I wish they just had a molecule draw button on this forum!
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Offline Borek

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Re: Trying a new synthesis-need the correct intermediate
« Reply #3 on: November 15, 2013, 04:42:05 PM »
I wish they read how to format their posts before complaining.

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