PREPARATION OF HINDERED ESTERS BY THE ALKYLATION OF CARBOXYLATE SALTS WITH SIMPLE ALKYL-HALIDES

Sterically hindered esters were prepared in excellent yields by the use of anion-exchange resins in both biphase and triphase systems. In addition, quantitative yields of a variety of esters were obtained by the displacement reactions of simple aliphatic and aromatic potassium carboxylate salts and alkyl halides in acetone or acetone-water mixtures. Esters prepared in quantitative yields include ethyl hexadecanoate in 95% acetone and ethyl 2,-4, 6-trimethylbenzoate, 1-methylheptyl 2, 4, 6-trimethylbenzoate, and ethyl 9, 10-epoxyoctadecanoate in pure acetone. The second-order rate constant for the reaction of potassium 2, 4, 6-trimethylbenzoate with iodoethane in 95% acetone was found to be 2.67 X 10-4mL-1s-1at 40°C. © 1979, American Chemical Society. All rights reserved.