Aspirin Synthesis Lab Report

The product was then suspended in 2 ml of water with a stir rod in a 50 ml Erlenmeyer flask and heated to boiling. Water was added in one milliliter increments until all the product was dissolved (18 ml added total). The saturated solution was allowed to slowly cool, and gradual white crystal formation was observed. Recrystallized product was collected once more by suction filtration with the Hirsch funnel once crystallization ceased. Collected product dried on a watch glass for a week, weighed 0.14 g (1.2 mmol), and the melting point was 139°-141°

Both Aspirin and the Unknown are soluble in dichloromethane, due to their non-polar characteristics. To separate the two components, sodium bicarbonate was added (see figure 3). Sodium bicarbonate reacted with aspirin and converted it to a salt, also forming water and carbon dioxide. It was observed that the solution "fizzed" when this reaction took place, showing the release of carbon dioxide. The newly formed salt then traveled to an aqueous layer where it was soluble, while the unknown remained in the dichloromethane layer. The two layers were then separated. To collect an aspirin solid, the combination of the addition of HCl and the process of vacuum filtration helped to break down the salt and form a solid. Then the solid was placed in the Fisher Scientific Biotemp Oven to dry it to a constant mass of 0.091 g, 32.97% of the total composition. The

Melting Point Data Table Compound Aspirin Caffeine Salicylamide Actual MP (ºC) 93 - 98 260 - 262 96 - 102 Expected MP (ºC) 135 236 140 Percent Error (%) ~30% ~12% ~30%

The isolation of aspirin, acetaminophen, and caffeine from Excedrin utilized the differing acidities and polarities of the three compounds. Extraction involved separating the three components by reacting them with HCL and NaOH, while thin layer chromatography involved separating the isolated compounds on a TLC plate. The binder was the first component extracted; followed by aspirin, acetaminophen, and caffeine was extracted last since it is a neutral and polar compound. The entire process can be seen in figure 1. The most utilized methods of extraction were gravity filtration and vacuum filtration which are displayed in figures 3 and 4 respectively. These methods were utilized to separate compounds based upon their differing

The mixture was heated at 120°C using an aluminum block and was stirred gently. After all of the solid dissolved, it was heated for 20 additional minutes to ensure the reaction was complete.

The solution was stirred with a boiling stick after a few drops, until the solution tests acidic with pH paper (red). Two more drops of hydrochloric acid were added to the solution. The liquid was removed from the reaction tube using a Pasteur pipette. To recrystallize aspirin, 3ml of water was added to the test tube, the mixture was heat until it was dissolved. Then, the solution was place in an ice bath to induce crystallization.

The purpose of experiment four was to synthetically prepare a sample of salicylic acid from methyl salicylate, also known as wintergreen oil. The salicylic acid formed is to be compared to salicylic acid synthesized from benzene and determine whether or not the two acids differ. This experiment occurs through organic synthesis, meaning in order to create the desired product, the starting material must be chemically modified.

By having a superior surface area of Aspirin tablets, the reaction occurred quicker. These predictions

The purpose of this lab was to synthesize aspirin, determine the theoretical yield, compare the percent yield to the theoretical yield and test the purity of aspirin by adding Iron (III) chloride to the product.

The goal of this experiment was to synthesize aspirin. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and acetic anhydride. In the reaction the hydroxyl group on the benzene ring in salicylic acid reacted with acetic anhydride to form an ester functional group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in the solution as well as some sulfuric acid, aspirin, and acetic acid. Crystallization, which uses the principle of

The expected acetylsalicylic acid product produced was 1.313g, therefore the crude percent yield calculated was 70.35% yield. This percent yield indicates that a high percentage of product was made, however the yield was not 100%, therefore loss of product was evident in the reaction process. Moreover, in the ferric chloride test, the salicylic acid and water, as well as the acetylsalicylic acid and water formed a dark purple color. However, acetylsalicylic was not supposed to react with ferric chloride and turn purple, because pure acetylsalicylic acid is not a phenol and therefore should not react. The melting point was determined to be 165 C and this is a higher melting point than the literature value of 135 C. The product of acetylsalicylic acid was obtained because a high yield was obtained, however the product was not pure and contained unreacted salicylic acid, because the ferric chloride test resulted in a purple color and the melting point determined was greater than the literature

Results: Reactions equations: Calculations: Substance M.W. Grams Moles Salicylic Acid 138.118 3 0.0217 Acetic Anhydride 102.09 6.48 (density=1.08 g/mL) 0.0635 Aspirin 180.157 3.91 (theoretical) 0.0217 (theoretical) m (salicylic acid) = 3g M.W (salicylic acid) = 138.12 g/mol n (salicylic acid) = m/ M.W = 3/ 138.12= 0.0217 mol n (salicylic acid) = n (aspirin) m ( expected aspirin) = n * M.W = 0.0217 mol * 180.16 g/mol = 3.909 g m ( experimental aspirin) = 3.09 g % yield mass= (m ( experimental aspirin) ×100%)/(m ( expected aspirin))

It was an effective medium in which aspirin hydrolysis could

This report presents the synthesis of Aspirin (acetylsalicylic acid), as the product of the reaction of salicylic acid with ethanoic anhydride under acidic conditions. Aspirin was purified through recrystallisation by vacuum filtration, followed by desiccation of the Aspirin crystal over silica gel. The percentage yield was calculated as 44.89% and a sample of Aspirin was analysed using infra-red spectroscopy and compared to the spectrum of pure Aspirin, this served as an introduction to the identification of functional groups in organic compounds. The melting point was calculated using an IA9000M apparatus and recorded to be 35.2°C, which was slightly below the melting point of pure Aspirin; known to be between 138-140°C. Both IR spectroscopy and melting point measurement were used verify the purity of synthetic Aspirin made, which proved to be fairly pure under these laboratory conditions.

3. A few drops of 6 M acetic acid were added until it became basic.