Dear Kimihiro Komeyama

suppose yo want to make sodium salt of carboxylic acid then you will have to add sodium hydroxide solution in equivlent amount to your carboxylic acid.

my question is that in place of sodium i want to keep an organic cation like tetrabutyl ammonium or tetraethyl ammonium,theN what should i have to do???

I have looked at your MS word document. This is very easy chemistry. Simply take the Na or K salt of a carboxylic acid (these can be made by cautious addition of sodium/potassium carbonate to the acid or perhaps can be brought). Next, it is just a case of performing a methathesis reaction with a [NR4][Cl] salt. These are commercially available. Now to avoid the metal impurity. If you make sure your starting Na or K salts are clean this will help and could easily be done by recrystallization. If you do the methathesis reaction in water (simply stir the two components overnight), and then repeatedly wash the aqueous solution with CH2Cl2 (three times) or diethyl ether, you will obtain a product that is free from metals. This could then be dried overnight on a Schlenk line to remove any water. Overall, this is the standard procedure to make ionic liquids, which can include ammonium salts such as those depicted in your word document. It would help if you use a very slight excess of the salts (1.05 equivalents) and these should not be carried into the non-polar phase.

I think u can go simply with Et3NH or like bases.

 To prepare an organic counter cation of a carboxylic acid or sulphonic acid dissolve acid in aque. soln. of NaHco3 in water & then remove the water by lipolisation to get solid salt with Na as a counter cation.

I request you to guide me in preparing K-salt of Indole Butryic acid. The purpose is that IBA is alcohol soluble whereas If convert this into salt it becomes soluble in water which has applications in propagation.