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Topic: How to add on a NO2 group and HSO3 group in the para position on a benzene?  (Read 8182 times)

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Offline inotamanhoe

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How to add on a NO2 group and HSO3 group in the para position on a benzene?
« on: May 04, 2008, 07:31:03 PM »
I am trying to figure out how to add to either a benzene, toluene, or acetanilide, so that my final product will be a benzene ring with an NO2 group and an HSO3 group in the para position.

I am guessing that i will use sulfonation of benzene, and nitration of benzene, but am not sure if either one of them can be a para director. Any ideas?
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Offline macman104

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #1 on: May 04, 2008, 07:38:36 PM »
KMnO4 will oxidize NH2 (which is a para director) to NO2, and I don't think the oxidation should affect your HSO3 group...although, I don't have any actual reference to back this thought up.
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Offline inotamanhoe

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #2 on: May 04, 2008, 08:11:30 PM »
So would it make sense to use Acetanilide as my starting reagent, and then sulfonate by using fuming sulfuric Acid (H2SO4) which would give me the HSO3 group in the para position on the Acetanilide and then go through with the Oxidation using KMnO4 to leave me with the final product?

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Offline macman104

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #3 on: May 04, 2008, 08:30:24 PM »
Why acetanilide?  Why not just aniline?
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Offline inotamanhoe

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #4 on: May 04, 2008, 08:34:07 PM »
Starting compound must be benzene, toluene, or acetanilide
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Offline macman104

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #5 on: May 04, 2008, 08:43:31 PM »
Yes, that would be fine, but you first need to cleave off the acyl group before you perform the oxidation.
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Offline inotamanhoe

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #6 on: May 04, 2008, 09:15:23 PM »
Im not sure on the best way to cleave off the acyl group.
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Offline macman104

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #7 on: May 04, 2008, 11:00:46 PM »
Acidic hydrolysis should cleave it and leave you with acetic acid and the free amine.
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Offline Yarr

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Re: How to add on a NO2 group and HSO3 group in the para position on a benzene?
« Reply #8 on: May 07, 2008, 06:28:42 AM »
Aniline cannot be oxidized to nitro benzene with KMnO4, because the ring is considerably activated. A much better reagent is DMDO in wet acetone.
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