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#Post#: 1563--------------------------------------------------
Organic synthesis question
DIR By: Michel
Date: December 14, 2012, 12:36 am
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What is the best route to synthesize 3-cyclohexyl-2-pentanone?
#Post#: 1574--------------------------------------------------
Re: Organic synthesis question
DIR By: hkar19
Date: December 14, 2012, 6:09 am
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i dont know exactly which way is the best one, we need to
compare them one-by-one first
but for synthesize, i think because we just have one functional
group here, we only have some option:
1. from alkene, and then you add H2O/H+ (or use some good
reagen, Oxy-demercuration)
2. from grignard reagent, from acetaldehyde with sec-butyl cyclo
hexane as the grignard's. then oxidize it with Pyridin
ChloroChromate
(i think we need add some chemical drawing here)
#Post#: 1578--------------------------------------------------
Re: Organic synthesis question
DIR By: Michel
Date: December 14, 2012, 12:10 pm
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How about; alkylating acetoacetic ester with chlorocyclohexane
and chloroethane succesively, followed by acid hydrolysis and
heating to decarboxylate.
Looks good on paper. Is this practical?
More replys(routes) please
#Post#: 2193--------------------------------------------------
Re: Organic synthesis question
DIR By: Potla
Date: February 25, 2013, 5:55 am
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On pen and paper, I got some ridiculous(and practically absurd)
routes:
1) Start with 2-pentanone. Treat it with Br2/AcOH to get
3-bromo-2-pentanone. Now treat this with Mg/ether to form the
grignard, and let it attack a mole of 1-chlorocyclohexane, which
should give the final product.
2) Start with 1-pentene. Treat it with NBS, followed by
H2O+PdCl2/CuCl2 (Br2/CCl4 followed by NaNH2/heat and H2SO4/HgSO4
would probably be much cheaper, lol :D ), which will give
3-bromo-2-pentanone again. Then proceed as in the last process.
I will see if I can come up with something more practical. :)
#Post#: 2200--------------------------------------------------
Re: Organic synthesis question
DIR By: Michel
Date: February 26, 2013, 2:10 am
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--- Quote from: Potla link ---
>
> On pen and paper, I got some ridiculous(and practically
absurd) routes:
> 1) Start with 2-pentanone. Treat it with Br2/AcOH to get
3-bromo-2-pentanone. Now treat this with Mg/ether to form the
grignard, and let it attack a mole of 1-chlorocyclohexane, which
should give the final product.
> 2) Start with 1-pentene. Treat it with NBS, followed by
H2O+PdCl2/CuCl2 (Br2/CCl4 followed by NaNH2/heat and H2SO4/HgSO4
would probably be much cheaper, lol :D ), which will give
3-bromo-2-pentanone again. Then proceed as in the last process.
> I will see if I can come up with something more practical. :)
>
--- End Quote ---
sounds good on paper, I only wonder how much bucks these
reagents get off a private scientist
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