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Topic: 4-hydroxyacetanilide from acetanilide  (Read 12921 times)

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Offline mark-sev

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4-hydroxyacetanilide from acetanilide
« on: March 05, 2009, 04:43:11 PM »
Sorry for asking this question, but i am just at the start of my organic chem course so i cannot answer myself this question, so i ask you how to synthetise 4-hydroxyacetanilide starting from acetanilide?

Thank you for the answers!

Offline macman104

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #1 on: March 05, 2009, 07:26:28 PM »
You first need to show an attempt.

Start with the first thing, what ways have you learned of to put an -OH on a benzene ring?

Offline nj_bartel

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #2 on: March 05, 2009, 07:40:36 PM »
I thought there was only the industry method of hydroxylating arenes - conditions too harsh to really use in a lab.

Offline macman104

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #3 on: March 05, 2009, 07:52:33 PM »
Nope, there is another way.  I'll give mark-sev some time to figure it out before I say it.

Offline russellm72

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #4 on: March 06, 2009, 05:06:44 AM »
Ok just a hint...

If you were to nitrate acetanilide then seperate the o,p isomers what FGI's could you do to make your title compound?

This is basic in the extreme but will give you a synthetic solution that can easily be undertaken in a lab.

any thoughts?

R.

Offline aldoxime_amine

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #5 on: March 06, 2009, 10:05:14 AM »
Ok just a hint...

what FGI's could you do to make your title compound?


Can you tell us what that means?

Offline sjb

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #6 on: March 06, 2009, 11:01:38 AM »
Ok just a hint...

what FGI's could you do to make your title compound?


Can you tell us what that means?

Functional Group Interconversion(s) - see e.g. http://preview.tinyurl.com/anrhmv

S

Offline mark-sev

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #7 on: March 07, 2009, 05:02:42 PM »
Well actually we haven't learnt anything yet about that....before we were learning about Sn1 and Sn2 reactions and eliminations and now we started electrophilic aromatic substitutions, but i guess this could not be the case since -OH is a nucleophile...i would have to look at some books maybe but i don't know if i will find it:D...i guess it's some oxidation or what, but i doubt that would be a very selective way...i'm really at the start of the curriculum...

Offline macman104

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #8 on: March 07, 2009, 05:16:36 PM »
Have you learned about the sandmeyer reaction, or maybe the term "diazonium" is familiar?  I'm pretty sure russellm and I are thinking about the same thing.

Offline mark-sev

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #9 on: March 10, 2009, 01:45:45 PM »
Nope, i haven't learned about that reaction yet, although i have heard somewhere that from this diazonium salts one can create alcohol group, so i see first one would need an amine group on place 4 on the benzene, so first i would have to make a 4-chloro derivate of acetanilide ( reaction with Cl2 in presence of FeCl3, or is there another way?), and then nucleophilic substitution with NH3, following sandmeyer reaction to diazonium salt and afterwards to alcohol (would this be feasible). Or not, since i found this reaction which involves some to me exotic catalysts: Buchwald-Hartwig reaction (link: http://en.wikipedia.org/wiki/Buchwald-Hartwig_reaction ).


Offline macman104

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #10 on: March 10, 2009, 03:19:29 PM »
Yes, that would be feasible (from a quick glance).  Easier to do would be to nitrate acetanilide, and then convert the NO2 group into NH2 and create the diazonium.  But that is what both russellm and I were getting at I believe.

Offline lutesium

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #11 on: March 10, 2009, 04:38:27 PM »
Why do you all go from DiAzonium route??? Halo-Benzenes can be easily converted to their -OH counterparts via a base and a Cu catalyst that's all :) !!!

Offline nj_bartel

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #12 on: March 10, 2009, 05:48:30 PM »
Don't you get a mixture of products and require harsh conditions by that route?

Offline lutesium

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #13 on: March 14, 2009, 11:53:22 AM »
Don't you get a mixture of products and require harsh conditions by that route?

No I dont think so. AFAIK An Iodobenzene can be formed by the route of KI3 (prepared instiu by reacting KI + I2) forming p and o but mainly p which thereupon be converted to -OH by reacting with KOH and a Cu salt or Cu alone. Forming primaily p which can be seperated by steam distillation.

Offline mark-sev

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Re: 4-hydroxyacetanilide from acetanilide
« Reply #14 on: March 16, 2009, 02:24:34 PM »
Replacing I- with OH- sounds to me like nucleophilic substitution?? Why is the name of the reaction you are proposing...Shouldn't electrophiles attack the electron-rich aromatic compounds...cause the carbocation made from benzene is highly unstable...correct me if i'm thinking wrong please.

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