Various combinations of reactions of methyl, n-butyl, allyl, and benzyl chlorides with sodium acetate or propionate, benzoate, and salicylate to form esters were studied in detail. In general, triethylamine was a very necessary catalyst for all the combinations. A cocatalyst, sodium-iodide, was required to achieve high yields of methyl and n-butyl esters. With the exception of allyl salicylate, the use of sodium iodide did not increase the yields of esters derived from allyl and benzyl chloride. Good to excellent yields were obtained at reaction temperatures of 75' to 175' C. and reaction times of 2 hours or less. HE preparation of esters from the reactions of alkyl chlorides T a n d sodium salts of carboxylic acids could be important if the sodium salt of the acid were inexpensive and readily
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