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Topic: P-Chlorobenzoic acid  (Read 3737 times)

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Offline Plumbum

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P-Chlorobenzoic acid
« on: May 12, 2015, 12:45:43 PM »
Hi

Can anyone tell me Now what side product could there be when synthesizing 4-Chlorobenzoic acid. I used 4-Aminobenzoic acid
It was a sand ever reaction.
There might be some language misunderstandings - I'm from Germany

Offline sjb

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Re: P-Chlorobenzoic acid
« Reply #1 on: May 12, 2015, 04:53:21 PM »
Hi

Can anyone tell me Now what side product could there be when synthesizing 4-Chlorobenzoic acid. I used 4-Aminobenzoic acid
It was a sand ever reaction.

What are the intermediates? How did you carry out the reaction?

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #2 on: May 12, 2015, 06:06:18 PM »
I first synthesized the diazonium compound by dissolving 4-aminobenzoc acid in water and hydrochloric acid.

Then I synthesized copper(1) chloride.

Then I mixed my dissolutions( Sandmeyer).
There might be some language misunderstandings - I'm from Germany

Offline pgk

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Re: P-Chlorobenzoic acid
« Reply #3 on: May 12, 2015, 06:29:02 PM »
Did you exceed the reaction temeperature above 5oC (mesured by a thermometer, in real time)?

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #4 on: May 13, 2015, 06:06:45 AM »
I dont think so IT was supposed to be between 0 and 5 degrees
There might be some language misunderstandings - I'm from Germany

Offline pgk

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Re: P-Chlorobenzoic acid
« Reply #5 on: May 13, 2015, 01:25:07 PM »
Then, a possible side product might be p-hydroxybenzoic acid by partial hydrolysis of the diazonium salt.
Also, note that above 5oC, the diazonium salt decomposes to benzoic acid and gaseous nitrogen that might be explosive. By the way, did you notice any bubbles formation in the reaction medium? 
« Last Edit: May 13, 2015, 01:50:59 PM by pgk »

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #6 on: May 14, 2015, 12:16:37 PM »
Thank you very much :)

What side products would you expect for the synthesis of antrillic acid ?
There might be some language misunderstandings - I'm from Germany

Offline pgk

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Re: P-Chlorobenzoic acid
« Reply #7 on: May 14, 2015, 01:05:12 PM »
Do you mean anthranilic acid?

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #8 on: May 14, 2015, 01:39:01 PM »
Yes i do, sorry!
There might be some language misunderstandings - I'm from Germany

Offline pgk

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Re: P-Chlorobenzoic acid
« Reply #9 on: May 14, 2015, 01:52:52 PM »
What is the structural difference between anthranillic acid and PABA?
Then, the answer is easy.

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #10 on: May 14, 2015, 02:07:46 PM »
Well the NH2 group is ortho in anthranillic acid and para in PABA
There might be some language misunderstandings - I'm from Germany

Offline pgk

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Re: P-Chlorobenzoic acid
« Reply #11 on: May 14, 2015, 02:18:19 PM »
So, what is the most possible side product of the synthesis of one of them?

Offline Plumbum

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Re: P-Chlorobenzoic acid
« Reply #12 on: May 14, 2015, 02:58:58 PM »
I don't know, the meta derivative?
There might be some language misunderstandings - I'm from Germany

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