[tellu]

PotassiumHey everybody, I am doing my Bachelor thesis on an organic synthesis. I was wondering if I were to add thionyl chloride (SOCl2) and dimethylformamide (together they form the Vilsmeier-Haack reagent) to 4-hydroxyphenylacetic acid, I would observe a polymerization reaction as the Vilsmeier-Haack reagent would convert the carboxylic acid into an acid chloride which could then be attacked by the remaining alcohol groups on the other molecules of 4-hydroxyphenylacetic acid.

The entire reaction I am trying to conduct involves the addition of triethylamine and a dimethyl formamide HCl salt to finalize the amidation reaction, however, adding the DMA.HCl has had no effect on the reaction mixture even though I would expect an exothermic reaction.

Thanks for the help in advance!

[rolnor]

The hydroxyl group will react with the wilsmeyer reagent as well. If you use 4-amino phenyl acetic acid plus dicyclohexylcardodiimide, DCC you could get some polymer I think. Use DCM as solvent

[labnet]

I think you should use pyridine as both acid binder and medium.  Mix socl2 and pyridine first. Once the smoke is complete, add the acid but slowly. Keep the environment as free from moisture and oxygen as possible.