Some properties of the ecgonines and their esters. VI. The calcium and lead salts of l‐ecgonine, the conversion of l‐ecgonine into l‐benzoylecgonine and its esterification with methyl alcohol and benzoic anhydride or benzoyl chloride

Abstract

AbstractThe calcium salt of l‐ecgonine is soluble in methyl and ethyl alcohols and also in anhydrous benzene. It crystallises in fine needles. Ecgonine forms a compound with calcium chloride.The lead salt also crystallises in needles and is readily soluble in alcohol and benzene.An almost complete conversion of l‐ecgonine into l‐benzoylecgonine is obtained in 5 days at ordinary temperature in aqueous acetone with the addition of 2–3 times the theoretical quantity of benzoic anhydride.By the action of benzoic anhydride and methyl alcohol on benzoylecgonine at ordinary temperature the anhydride of benzoylecgonine is formed as the main product, which can then give cocaine and benzoylecgonine with methyl alcohol. The conversion into cocaine obtained, however, by using 7 times the theoretical quantity of benzoic anhydride was only 80%.Benzoylecgonine when treated with methyl alcohol and 3.5 times the theoretical quantity of benzoyl chloride at ordinary temperature gives an almost complete conversion into cocaine.