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Topic: How could I synthesize m-nitrotoluene?  (Read 3832 times)

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Offline nj112233

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How could I synthesize m-nitrotoluene?
« on: March 28, 2011, 02:50:29 PM »
How could I synthesize m-nitrotoluene?  NO2 is meta directing, but does not allow alkylation and an alkyl group is ortho and para directing.  
« Last Edit: March 28, 2011, 03:06:05 PM by nj112233 »
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Offline Honclbrif

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Re: How could I synthesize m-nitrotoluene?
« Reply #1 on: March 28, 2011, 03:34:05 PM »
Do you have to start from nitrobenzene or toluene? If you can add functional groups can take them away too? Is there another functional group which would would add a nitro and a methyl in the correct orientation to itself and each other?
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Offline nj112233

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Re: How could I synthesize m-nitrotoluene?
« Reply #2 on: March 28, 2011, 03:46:14 PM »
I have to start with benzene.  I'm not sure if I could then add ClCH2C=O/AlCl3, then HNO3/H2SO4, then H2/Pd and then somehow selectively oxidize the NH2 group to NO2 without oxidizing the alkyl group
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Offline AWK

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Re: How could I synthesize m-nitrotoluene?
« Reply #3 on: March 30, 2011, 03:40:45 AM »
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Offline nj112233

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Re: How could I synthesize m-nitrotoluene?
« Reply #4 on: March 30, 2011, 04:07:25 PM »
Thank you!
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