Multi Step Synthesis Of Aspirin

From the vial labeled “AE,” aspirin (0.533 g) was placed into a 50 mL Erlenmeyer flask with a boiling stick. Toluene (20 mL) was brought to a boil on a hot plate. The boiling toluene (10 mL) was then added to the aspirin until the solid dissolved completely. After allowing the solution to reach room temperature, the solution was placed in an ice bath for 16 minutes. After the crystals

Separation and Purification of the Components of an Analgesic Tablet. Cora Bruno, Lab Section E. Aspirin, Caffeine and Acetaminophen were separated from four analgesic tablets of Excedrin using extraction techniques. 5% wt/vol NaHCO3, 4M HCL, ethyl acetate and deionized water were used to separate the three active components. MgSO4 was used to dry each extraction. Aspirin was isolated using a hot water bath and weighed to determine the percent theoretical recovery and the actual percent recovery of aspirin. After separation, Aspirin (ASA), Caffeine (CAF), and Acetaminophen (ACE) were purified and identified using Thin Layer Chromatography (TLC). Standards and purified ASA, CAF, and ACE were spotted on the silica gel (stationary phase) of the

In experiment two, the drug Panacetin was separated by a series of chemical reactions into its three components: sucrose, aspirin, and an unknown active ingredient, either acetanilide or phenacetin. The purpose of this lab was to determine what percentages of each component is present in the pain-killer. The initial step was to dissolve Panacetin in dichloromethane. However, sucrose is insoluble in dichloromethane because organic molecules are soluble in organic solvents, and dichloromethane is an inorganic solvent, so only aspirin and the unknown dissolved. By using gravity filtration, sucrose was filtered from the solution and 0.30g of solid was collected.

The synthesis of acetaminophen involves the attraction of the electrophilic carbonyl group of acetic anhydride to the nucleophilic NH2

3.0g of salicylic acid was weighed then 3.0mL of acetic anhydride and 6 drops of 85% H3PO4 were added to it. The mixture was warmed over a water bath for 5 minutes while stirring. After warming, 20 drops of distilled water was slowly added. 15mL of water was added then the solution was heated until it became clear. It was allowed to cool and was placed in an ice bath until the solution becomes cloudy. Using pre-weighed filter paper, the mixture was filtered and was allowed to dry in the filter paper.

Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. The phenol group that will attack the carbonyl carbon of the acetic anhydride is the –OH group that is directly attached to the benzene since it is more basic than the –OH group attached to the carbonyl 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. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in

Ever wonder about the chemical makeup of tablets that people take for pain relief? Before a tablet can be successfully made, the limiting and excess reactants must be considered. The limiting reactant will affect the amount of the product that can be made. Another reason why the starting reactants must be determined carefully is to make reduce the amount of the reactant in excess so that reactants are not wasted. This experiment uses an Alka-Seltzer tablet. Alka-Seltzer dissolves in water and is an antacid and a pain reliever1. The Alka-Seltzer tablet has many uses such as relief of headaches, ingestion, heart burns, or even upset stomachs2. The active ingredients in an Alka-Seltzer tablet is aspirin, also known as acetyl-salicylic acid (C8H12O4), citric acid (C6H8O7), and sodium bicarbonate (NaHCO3)2. The aspirin in the Alka-Seltzer tablet helps with pain relief. Because of the acid-base chemistry (Brønsted-Lowry), citric acid and sodium bicarbonate produce O2, which makes the tablet fizz when it is dropped in liquid. The Brønsted-Lowry theory shows how the Brønsted-Lowry acid donates a hydrogen ion while the Brønsted-Lowry base accepts the hydrogen ions3. The remaining NaHCO3 that is in excess post reaction with the citric acid is what is used to neutralize stomach acid which helps relief heart burn2. The problem in

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

Industrial production of Aspirin is dependent on the company producing the drug; however the general method of production is known as slugging or dry-granulation. In this method, corn starch is mixed with pure water and is then heated and

I hypothesize that salicylic acid will react with acetic anhydride to produce acetylsalicylic acid (aspirin) and acetic acid (vinegar).

The purpose of the lab was to synthesize aspirin and oil of wintergreen, and to determine its purity using recrystallization process, determining its melting point and using back-titration. To synthesize aspirin, salicylic acid and anhydride was used to drive the reaction to completion. In the synthesis of oil of wintergreen we reacted salicylic acid and methanol to produce methyl salicylate. This reaction is an example of a condensation reaction where the carboxylic acid and alcohol group combine to form an ester. In producing aspirin, we wanted to obtain the purest form, so we removed impurities such as unreacted salicylic acid and acetic acid. Acetic acid was removed by rinsing the sample in water because acetic acid is soluble in water. Salicylic, however, was removed by using the recrystallization process because it is insoluble in water. To recrystallize, we dissolved a sample of crude aspirin in warm ethanol and let it cool. Because aspirin is less soluble in ethanol than salicylic acid, it will crystallize out of the solution. To obtain the purified aspirin sample, we then filtered the solution to separate it from the impurities. To determine qualitatively the purity of the recrystallized aspirin, we determined its melting point using a melting point apparatus. Using the idea of freezing point depression, the presence of impurities will lower the melting point of the substance. Thus, by comparing the melting point to the actual

The scenario for this experiment is to determine the chemical structures for two “new” compounds called Acetaminophen and Ibuprofen. In order to determine the structures of these compounds, we will utilize three different instruments that will create spectra that will be analyzed in order to determine the structures of the compounds. The instruments that we will use for this experiment include Gas Chromatography Mass Spectrometry (GC/MS), Infrared Spectroscopy (IR), and Nuclear Magnetic Resonance Spectroscopy (NMR). Each instrument provides information that can be combined in order to determine the specific characteristics and functional groups that will lead to structural determination.

Chemical synthesis is an imperative technique most relevant to organic chemists. Synthesis employs a succession of chemical reactions by using pre-existing structures to make new and functional ones. A combination of lab techniques could be developed in order to synthesize and attain the desired product. This particular experiment calls for the use for reflux, extraction, recrystallization, infrared spectroscopy, and melting point analysis. The overall objective of this lab is to utilize these steps to synthesize acetaminophen from p-aminophenol and characterize it .

During the 1890s Felix Hoffman a chemical engineer who worked at the Bayer Company located in Germany was looking to help his father who was suffering from arthritis.  He discovered how to isolate acetylsalicylic acid in a digestible form.. Starting in 1899, the Bayer company began to sell an aspirin powder to doctors to provide to their patients. The drug became a hit and, in 1915, it was sold as over-the-counter

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.