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Author: Subject: chlorination of benzene
CrossxD
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[*] posted on 19-11-2015 at 10:24
chlorination of benzene


is possible to do chlorination of benzene with AlCl3 without any special condition?
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Pumukli
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[*] posted on 19-11-2015 at 11:48


Depends on how do you define "special condition".

It does not require microwaving, sonication, UV, VIS, IR, etc. lighting, no high-voltage discharge either.

But does require anhydrous reagents because AlCl3 is water sensitive.

The emitted HCl gas can cause unease in a (shared) kitchen environment, so proper venting is also useful.

Might require temperature control, depending on mass of materials used.

Why not consult e.g. Vogel or maybe Org.Syn. for a proper description of the process. Wait! They may not use AlCl3 but FeCl3 instead (or something similar), the quirks are roughly the same.
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Detonationology
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[*] posted on 19-11-2015 at 11:54


Here's what I found
Screen Shot 2015-11-19 at 2.52.44 PM.png - 60kB

[Edited on 11-19-2015 by Detonationology]




“There are no differences but differences of degree between different degrees of difference and no difference.” ― William James
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CrossxD
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[*] posted on 22-11-2015 at 04:12


and is possible to chlorinate toluene to benzyl chloride react it with potassium cyanate and chlorinate benzyl cyanide in pozition 4?

[Edited on 22-11-2015 by CrossxD]
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JJay
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[*] posted on 22-11-2015 at 05:42


Hmm I have a big bag of FeCl3... I bought it for something else (and only needed a small quantity), but it might be fun to put some groups onto benzene rings.
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kecskesajt
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[*] posted on 22-11-2015 at 06:25


But you could easily chlorinate with TCCA! Discussed on the site several times.
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Metacelsus
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[*] posted on 22-11-2015 at 09:31


Quote: Originally posted by CrossxD  
and is possible to chlorinate toluene to benzyl chloride react it with potassium cyanate and chlorinate benzyl cyanide in pozition 4?


You'd need KCN, not KCNO.




As below, so above.
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Pumukli
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[*] posted on 23-11-2015 at 12:04


Quote: Originally posted by JJay  
Hmm I have a big bag of FeCl3... I bought it for something else (and only needed a small quantity), but it might be fun to put some groups onto benzene rings.


If it is in a bag then chances are it is unsuitable for this purpose. Not because of the packaging material but I doubt that anhydrous ferrichloride would survive in a plastic bag too long. If it is orange colored then it is unsuitable (hydrated). If the color is black and the powder is obviously dry, then you are lucky.
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JJay
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[*] posted on 23-11-2015 at 12:20


It's black and appears dry.... I keep it triple bagged.
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UC235
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[*] posted on 23-11-2015 at 13:32


Adding some degreased steel wool is quite sufficient to form fresh, high-surface area FeCl3 in-situ. It works well with benzene bromination and I'm sure it would work with chlorination (though I personally loathe working with gaseous chlorine).

[Edited on 23-11-2015 by UC235]
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