May 25, 2020, 01:49:27 AM
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Topic: Produce chloroacetyl chloride from monochloroacetic acid (Experimental Procedure  (Read 4928 times)

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Offline aliaja

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I am working on the proposal of a synthetic route to choroacetyl chloride. Literature I've read suggests the phosphogenation of of chloroacetic acid, the reaction of thionyl chloride with chloroacetic acid and the chlorination of acetyl chloride. I was leaning toward chlorination, but am not entirely certain which one would work best. I also was wondering if anyone knew where in the literature I could find a lab procedure explaining how to carry out this experiment

Offline discodermolide

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Several things: I would leave this alone a) do not go near phosgene, b) chloroacetylcloride can act as a sensitiser in some people and cause very bad symptoms, c) furthermore it is very potent lachyramator, d) you don't want to handle chlorine either, e) thionyl chloride is also not a very pleasant chemical, f) probably none of the methods you suggest would work  and last but not least g) you can buy it.
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Offline BobfromNC

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I would not use phosgene if not essential, and chloronating anything alkyl is not for small scale lab work.   So that leaves the reaction of thionyl chloride with chloroacetic acid as a reasonable way to do this.   

And yes, this is not a great chemical to work with, and there are better reagent/procedures for most any reaction that chloroacetyl chloride can do, so make sure that it really is the only way to go. 

Thionyl chloride is used commonly in labs to make acid chlorides, and works well, but is certainly noxious.   But at least it is an easy reaction, you add it to the acid in DCM, toluene, or another appropriate solvent, reflux, and then evaporate off the solvent and excess thionyl chloride and the resultant material should be your chloroacetyl chloride, although it may boil near the temperature of thionyl chloride, so check that first.

And buying it is certainly the way I would go.

Offline Dan

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And buying it is certainly the way I would go.

I'll third this.

Chloroacetyl chloride is very cheap. True, chloroacetic acid is cheaper, but once you factor in buying reagents, solvents, electricity and your time it should be clear that making it yourself is a complete waste of money. Why are you doing it?
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