I'm trying to sulfonate diphenic acid using trimethylsilyl chlorosulfonate to obtain a water soluble form of diphenic acid by forming the corresponding sodium or potassium salt. I tried using the procedure described by the Ivan et. al in 2017 (DOI: 10.1039/c7sc00430c). But it is not working for diphenic acid. Could anyone suggest or direct me to a procedure that I can use for the sulfonation of diphenic acid using above reagent ?
In your above mentioned journal, the preparation of sulfonate derivatives are carried out at high temeperature in dioxane medium. You can try this reaction at low temperature. A reference is attached herewith. But this reagent is used for the synthesis of cyclic sulfates. You can get some clue from here.
It can be carried out in dry methylenechloride as solvent at room temperature. This reaction is terminated using equivalent amount of diluted acidic solution. After isolation of the crude solid, you can try to form the corresponding sodium or potassium salt. A reference link is presented below.
https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=2&ved=0ahUKEwjV54mqtMHTAhWCMBoKHVbTBvwQFggsMAE&url=http%3A%2F%2Fwww.arkat-usa.org%2Fget-file%2F52695%2F&usg=AFQjCNGiMC9SqjNSDAokMrxJgdXLq2fXGw&sig2=Puxlpzhk8-a4OMcPRkOnkA&cad=rja
Hello all,
Thank you for very much for your answers. The issue is I can not use DCM as my solvent for the reaction as diphenic acid is no soluble in DCM even though it is soluble in dioxane.
the carboxylic acid may be interfering with the trimethylsilyl chlorosulfonate. Try making the ester
Rather than an ester, which will need to by hydrolyzed, you could work with the acid chloride. Dissolve diphenic acid in an excess of thionyl chloride (stir overnight, add catalytic DMF if necessary), strip off thionyl chloride, dissolve residue in DCM, and proceed.
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