The reaction shown above outlines the synthesis of the lupinine ester. These esters have been studied for their biological properties. Found mainly in plants there is heavy research being done on them for their antiviral, antitumor and hepatoprotective activity. In some cases lupinine esters can exhibit local anesthetic properties.
The reaction shows how you would synthesize a lupinine ester from betulonic acid chloride with lupinine. Side conditions for this reaction include the presence of triethylamine and must be performed in dry CCl4.
The most common medical ester is aspirin (ASA; acetyl salicylic acid). Other drugs such as Worm Guard (anti-wormer), Maxicaine (local anesthetic), Malathion (organophosphate), Mebendazole (antihelmenthic), Demerol (narcotic analgesic) and Equinil (sedative) are also esters.
The starting reactants for this experiment are salicylic acid and acetic anhydride (structures are shown above).
Salicylic acid reacts better with acetic anhydride than acetic acid, so acetic acid will provide the acetyl group which will react with the alcoholic -OH group on the salicylic acid. (The reaction is on the top of the post.)
Chemicals needed for the reaction: Salicylic acid, Acetic anhydride, and Concentrated sulfuric acid.
Equipment: 250 mL Erlenmeyer flask, Hot water bath, Ice bath, Buchner funnel and filter paper, Glass stirring rod, and Electronic pan balance and weighing boat.
