Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Chris_Whewell on January 22, 2005, 01:14:09 PM
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I need to produce azelayl monochloride. As you know, azelaic acid is a nine-carbon linear aliphatic dicarboxylic acid. I need the monoacyl halide.
A reference to a prep would be very helpful.
I attempted adding 0.1 mol azelaic acid to toluene; unfortunately the solubility of azelaic in toluene is limited. Nevertheless, I added 0.1 mol thionyl chloride to the mixture, followed by the addition of a tertiary amine. There was a slight exotherm, up to about 45 C. However, things are not looking very nice. Perhaps a different solvent ?
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I think that usually these reactions are done with dichloromethane solvent and a catalytic amount of N,N-dimethylformamide (DMF). When I have made acid chlorides this way, the reaction is usually very clean (although I would usually use oxalyl chloride in stead of thionyl chloride.
At any rate, it might be difficult to get the mono-acid chloride. I would susupect that you would get a statistical mixture of products.