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Author: Subject: Synthesis of Resorcinol
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[*] posted on 7-4-2006 at 23:37
Synthesis of Resorcinol


Resorcinol has plenty of uses in organic chemistry, including the synthesis of styphnic acid, So I

decided to do a little research on it's possible synthesis. Here's what I found:

1. By fusing many resins (galbanum, asafoetida, etc.) with Potassium Hydroxide
2. By fusing 3-Iodophenol with Potassium Carbonate
3. By fusing phenol-3-sulfonic acid with Potassium Carbonate
4. By fusing benzene-1,3-disulfonic acid with Potassium Carbonate
5. By the action of Nitrous Acid on 3-aminophenol
6. By the action of 10% HCl on 1,3-diaminobenzene

Many ortho- and para-compounds of the aromatic series (for example, the bromophenols,

benzene-para-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide.

Is it possible to do any of the above methods in a home lab?
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Sergei_Eisenstein
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[*] posted on 8-4-2006 at 01:07


I think the easiest approach to resorcinol involves a Sandmeyer-type reaction (not to be confused with the notorious Sandmeyer terrorizing some parts of this board ;) ). The reactants are rather simple and the reaction can be done in a home lab. For resorcinol, several approaches can be thought of, but one option goes like this:

m-dinitrobenzene > m-phenylenediamine > resorcinol

Nitration of nitrobenzene (or dinatration of benzene) preferentially yields m-dinitrobenzene, so the substituents are in the desired position (though you might need fuming nitric acid). Reduction of this compound will result in m-phenylenediamine, which in turn will yield resorcinol after a Sandmeyer reaction. My personal preference would be a Sandmeyer reaction rather than fusing reactants at high temperature. Sandmeyer reactions have to be kept cold (0-5°C).

Quote:
6. By the action of 10% HCl on 1,3-diaminobenzene


It's best to consider hydrogen sulfates because there can be competition from the nucleophilic chloride. Not only may your yields drop, but the work-up might be more difficult as well.

[Edited on 8-4-2006 by Sergei_Eisenstein]
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[*] posted on 11-3-2011 at 03:23


Is there some easy way to prepare 3-aminophenol from phenol or something similar?
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[*] posted on 11-3-2011 at 16:48


Hydroxylation of benzamide followed by the Hofmann degradation. There may be an easier method known to those of the art
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DJF90
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[*] posted on 11-3-2011 at 17:22


Hydroxylation of benzamide how?
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[*] posted on 11-3-2011 at 18:48


Quote: Originally posted by DJF90  
Hydroxylation of benzamide how?


Fenton - Udenfriend maybe?




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[*] posted on 12-3-2011 at 00:10


When using Fentons Reagent to oxidise benzene to phenol how does one actually go about this?
Benzene and hydrogn peroxide and immicible and you cant reflux as this would decompose the hydrogen peroxide rapidly... has anybody got a write-up of this reaction?
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[*] posted on 12-3-2011 at 00:53


Quote: Originally posted by Picric-A  
When using Fentons Reagent to oxidise benzene to phenol how does one actually go about this?
Benzene and hydrogn peroxide and immicible and you cant reflux as this would decompose the hydrogen peroxide rapidly... has anybody got a write-up of this reaction?

Fenton's reagent has nearly no use in preparative chemistry. I don't know where you got that from, but only very few cases of actual application in preparative chemistry exist. One such example is described in Organic syntheses. Most substrates generally give products that are more susceptible to further radical reactions than the starting material itself.




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[*] posted on 25-1-2018 at 05:28


I couldn't find a better thread for this. I'm considering the sulfonation of resorcinol at the ortho site. I've read that the sulfonation of phenol is a thermodynamically driven reaction. The sulfonic acid first attaches to the ortho site and then at higher temperatures it attaches instead to the para site. How much does this carry over with resorcinol? Does steric hindrance show up in the second diol? Chemistry texts from a century ago seem to show that the sulfonic acid is a para group in resorcinol.
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[*] posted on 25-1-2018 at 14:54


Hi roXefeller:

I can't answer your question but I know a man who can:

http://dlx.b-ok.org/genesis/1129000/aeabbd8ad915ff118caa872ccfde9438/_as/[Hans_Dressler_(auth.)]_Resorcinol_Its_Uses_and_D(b-ok.org).pdf

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[*] posted on 25-1-2018 at 16:34


I have made resorcinol from m-disulfonic acid. This is challenging as you have to do a caustic fusion and the yield is very low. I have posted on this.

I am very close to making catechol from guiacol. But this is of no help for you.




The single most important condition for a successful synthesis is good mixing - Nicodem
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