Dear Colleague
I need your advice, I am planning to synthesis some derivative of the Nicotinic acid, Ferulic Acid and Caffeic acid, so how can I synthesise acid chlorides for this compounds like nicotinoyl chloride....?
Hi Mihamed,
The following link should be helpful:
http://www.commonorganicchemistry.com/Rxn_Pages/Acid_to_Acid_Chloride/Acid_to_Acid_Chloride_Index.htm
Dear Mohamed Assaleh
First, to save your time and effort you can purchase the acid chloride which is available in sigma. (nicotinic acid chloride). But if you are planning to save money and prepare the acid chloride your self there are several methods previously reported. I have tried the first pathway myself and it was successful.
[A] https://pdfs.semanticscholar.org/6fff/4fcbcb06382927bd4c1cd07498b241706076.pdf
[B] http://www.prepchem.com/synthesis-nicotinoyl-chloride/
[C] http://rasayanjournal.co.in/vol-2/issue-2/26.pdf
Note,
it is necessary to use fume hood because of the liberated gases (SO2, HCl)
IF you are planning to react these acid chlorides with a strong nucleophile or amine you can try the preparation or the ester which react smoothly and slowly
Good Luck
Thank you all for your reply,
yes of course I am using fume hood and I tried before with Thionyl chloride /THF but was not good, Thionyl Chloride/ DMF which i was not satisfied of the result because after re-crystallization it didn't give me good FTIR spectra.
To the schemes above. The hydrogen chloride formed in the reaction leads to the formation of nicotinoyl chloride hydrochloride. My recommendation for free base of nicotinoyl chloride preparation. Dissolve 1 eq of KOH (s) in methanol, add 1 eq of nicotinic acid. Evaporate the methanol to dryness. You get 1 eq of the potassium salt of nicotinic acid. Overlay the salt with an excess of thionyl chloride, add 2-3 drops of DMF. Heat under reflux for about 3 hours. Add the same volume of dry toluene, or xylene. Filter off the KCl, wash with toluene. Evaporate the combined filtrates to dryness. The product, free base of nicotinoyl chloride, is suitable for further syntheses without purification. Do not purify!
Use anhydrous benzene as solvent in Nitrogen atmosphere and chilled condition (ice bath) and slowly add oxalyl chloride.
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