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.
In the syntheses of aromatic esters and ethers, CsF-Celite has been found to be a very efficient, convenient and practical reagent. In fact, it is used for the coupling reactions of a number of aromatic and heteroaromatic phenols with alkyl, acyl or benzoyl halides.
Many other organic reactions have recently been catalyzed by CsF-Celite, such as the reactions to synthesize carboxylic esters, γ-lactones, N-alkylation of anilines, or carboxamides.
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.
Let’s look at some chemical structures:
One problem occurs with aspirin is that it has a destructive effect on the blood vessel walls and inhibit the synthesis of prostacyclin. To resolve this problem, we can use potential anti-platelet agents including the O-acyl esters which are synthesized from salicylic acid and diflunisal. Those agents work by acylation of cyclooxygenase and have a higher extraction than aspirin. That makes them yield a greater selectivity in their effect on platelet inhibition relative to prostacyclin inhibition on vessel walls.
The actual reaction is shown on the top.
