Tried different combinations such as Mitsunobu reaction, DMAP-DCC, DABCO-DCC, TEA, DIPEA, SmCl3 (Lewis acid) in solvents toluene, DCM, THF etc.
You could try to convert your carboxylic acid into the corresponding acyl chloride (SOCl2 or (COCl)2/DMF) and then add your alcohol upon it.
You could try to convert your carboxylic acid into an acyl chloride using the Ghosez's reagent. I used this technique on various systems to create amide bonds and esters. It is very mild and super easy to handle and work-up.
Use para-toluenesulfonic acid as catalyst in 2-5% mol in THF or chloroform at r.t. Or slight reflux. Finally evaporate all volatiles add hexanes to separate catalyst and from the hexanic fraction you can isolate your desired product. Hope this helps.
I agree with Mr.Anil ,you can do esterfication of the carboxylic acid with alcohol using Dean stark process by Toluene or any isotropic solvents. good luck
Esterification reaction can be tried with acidic resins also like amberlite, indian resins, previously i have tried and succeeded the preparation of methyl ester of corresponding acid.
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