Dear Raja,

I suspect that you have decomposed the ester forming acetic acid and salicyclic acid and/or their TEA amides/salts as reported as follows (L.J. Edwards, Bull. Soc. Chim (15) 1914)

Dear Larry,

Thanks for your quick response. but I could not find this reference. please send me its complete reference or send me this article to my email if you have it. my email is [email protected]

Thanks you.

Dear Raja,

If I understood you well, you attempted to make the triethylammonium salt of aspirin via reacting neutralization the free carboxylic acid of aspirin with the base triethylamine. If this salt is formed, it should ve very stable in anhydrous conditions, however, as you stated the solution color was changed presumably as a result of a decomposition of the aspirin salt. This decomposition is likely to occur if moisture (water) or any other nucleophile is present. Water can attack the acyl group of the aspirin salt to fernish salicylic acid and triethylammonium acetate (ester hydrolysis reaction). Therefore, I suggest that you repeat the reaction, however, with super dry conditions to avoid any hydrolysis (the reaction solvent should be very dry). Pleaser note that you CAN NOT use methanol or ethanol as solvents since both can act as nucleophiles. I suggest that you use dry THF, dry dioxane or dry DCM. When you repeat the reaction maitain the temperature such that will not exceed RT.

I suggest that you first check what product do you have. It might be that you have the desired product (triethylammonium salicylate) with a slight yellowish impurity.

Hoping this will be helpful,

Rafrik