Laboratory 5: Synthesis of Organic Compounds
Introduction:
In this experiment, aspirin will be synthesized from salicylic acid using acetic anhydride. The sodium salt was initially prescribed for its antipyretic and analgesic effects, but the salt was too irritating to the stomach, so a phenyl ester version was developed as a replacement. The esterified version passed successfully through the acidic stomach without irritation. It was hydrolyzed in the basic environment of the intestines, producing poisonous phenol. To avoid this problem, acetylsalicylic acid, where an ether is instead formed by the reaction of the alcohol group of salicylic acid with acetic acid, is used now. Acetylsalicylic acid, better known
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Then, heat the system on a hot plate for about 15 minutes after the water begins to boil gently. If the solid does not dissolve, heat for an additional 10 minutes, stirring as necessary. Next, Remove the flask and add 25 mL of ice water to the flask to decompose any unreacted anhydride. Then sit the flask in a beaker of ice until crystallization is complete. Next, separate the crystals from the liquid by suction filtration. Wash the crystals well with water, breaking up large chunks. Then leave the crude crystals to dry on the suction filter while you perform the experiment in part B. Measure the crude yeliend and make additional observations about the nature of the crystals. Next, recrystallize the crude aspirin by dissolving the crystals in a small amount of ethanol in a small beaker. Heat the solution to boiling. All crystals should eventually dissolve when boiling is reached. Carefully remove the beaker from the hot plate and allow to cool to room temperature. Promote further crystallization by cooling in an ice bath. Then, use the suction filtration apparatus again to filter the crystals. Use some water to wash if necessary. Allow the crystals to dry, breaking up any lumps with a spatula. Then, measure the melting point of the aspirin and compare with that of salicylic acid and pure acetylsalicylic acid. Place any leftover product into the designated waste container. For the preparation of oil of wintergreen in a green small beaker add
In this experiment the concentration of acetyl salicylic acid (ASA) in an aspirin tablet will be determined. This can be done by dissolving a tablet in a strong base, NaOH, and titration it with a strong acid, HCl. The quantity was found to be about 75.5% of the weight of the tablet, or about 318 mg per tablet. This value tells the pharmaceutical companies how much to state the recommended dosage as based on how much ASA is needed to feel the headache and pain resistant effects. Also it can be used to state precautions for the customers based on the known LD50 value (200 mg/kg).
The vial was removed from the heat and cooled to room temperature. The spin vane was rinsed with 2-3 drops of warm water over the conical vial. The vial was cooled to room temperature then placed in an ice bath for 15 minutes. The liquid was decanted from the mixture and the resulting crystals were dried on filter paper. The crystals were then placed on a watch glass for further drying. The crystals were weighed and a small sample was placed into a capillary tube for melting point determination.
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.
Results and Discussion Synthesis of Compound 3. Scheme 1: Synthesis of Compound 3. To synthesize compound 3, an approach involving treating triptolide with dimethyl sulfide and benzoyl peroxide in acetonitirile was used (Scheme 1). This approach resulted in the formation of compound 4 with a 51% yield and in triptonide (5) with a 46% yield.
Write down if its Soluble(S),slightly soluble(SS), or Insoluble(I). Next, with cyclohexane as the second solvent. Obtain 7 test tubes and label them with the name of solutes: acetone,water, dichloromethane,acetonitrile ,glucose,benzoic acid and oleic acid. For the solutes, either weigh out 0.05g of solids or add 10 drops of liquid into the test tubes. Add 1 mL or 20 drops of cyclohexane to each test tube and stir. Note down the observations in the second table. Write down if its Soluble(S),slightly soluble(SS), or Insoluble(I). Thirdly, obtain 7 test tubes and label them with the name of solutes: acetone,cyclohexane,water, glucose,benzoic acid,sodium sulfate and oleic acid. For the solutes, either weigh out 0.05g of solids or add 10 drops of liquid into the test tubes. Add 1 mL or 20 drops of acetonitrile to each test tube and
It has been documented that substance P interacts with peroxisome proliferator- activated receptors- gamma (PPAR-γ). Substance P decreases the level of PPAR γ that reduces the survival of neurons.[8] PPAR- γ decreases the level of proinflammatory mediators[9], increase development and growth of brain size and increase level of choline acetyltransferase (ChAT) expression.[39] ChAT is involved in synthesis and formation of acetylcholine by catalyzing the transfer of an acetyl group from the acetyl-CoA to choline yielding acetylcholine (ACh).[10] Substance P decreases the PPAR-γ level which upregulate inflammatory mediator level and reduces synthesis and formation of acetylcholine resulting in neurodegeneration.
Acetylsalicylic acid, or also known as aspirin is known to be a drug that relives people of pain and is commonly used even today. It is synthesized from salicylic acid and ethanoic anhydride, both of small quantities. Phosphoric acid was used as a catalyst in the synthesis to speed up the process. Esterification is involved and the final product is aspirin with the presence of acetic acid as the byproduct. In order to create the powder form of aspirin, the process of crystallization was conducted and was run through vacuum filtration. After running through the help of an electronic instrument, the result that was achieved in this experiment was met due to
antioxidant enzymes including small-molecule-weight antioxidants depends on cellular redox environment as it is a delicate process to regulate the two. ROS are responsible to regulate several physiological actions such as the ability to mediate and relate signal transduction from membrane receptors, At low concentrations, ROS are involved in regulating several physiological actions, including their ability to mediate relate signal transduction from membrane receptors, thus aiding the stimulation of several proteins and enzymes (1,2). Conversely, accumulation of extra intracellular ROS lead to oxidative stress, in turn will impair cellular membranes, promoting mitochondrial injury and cell death, which adversely impacting upon cell function and survival 3,5)
For this work, all the chemicals were used an analytical grade, and as received without additional purification. All aqueous solutions were made by using high purity deionized water with a resistivity (ρ) 18 MΩcm-1. Silver Nitrate (AgNO3, 99.0%), Copper (II) Sulfate Pentahydrate (CuSO4.5H2O, 99.0%), Povidone (PVP- (C6H9NO)n, 99.0%), Sodium borohydride (NaBH4, 99.0%), and Absolute Ethanol (C2H5OH,
For this purpose, to optimize the reaction conditions for the synthesis of compound 3a, the condensation reaction of benzaldehyde (1 mmol) and 2-naphthol (2 mmol) was test using different amounts of silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride as a Brønsted acid ionic liquid catalyst under solvent- and metal-free conditions at ambient temperature (Table 1). As it can be seen in Table 1, when reaction was carried out in the absence of the silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride, after 120 minute the reaction was without yield of product (Table 1, entry 1). The best results were achieved when 20 mol% of the silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride was appropriate to promote the
This series of labs aimed to synthesize and characterize aspirin from salicylic acid and acetic anhydride. The synthesis and recrystallization procedures entail the production and purification of aspirin. Several characterization techniques utilized in order to test its purity. Methods to characterize purity include determining the melting point of pure and crude aspirin, the pH
Aspirin is a commonly used pain killer and an anti-inflammatory. Hagiwara, Kaneko, Murata, Ikegami, and Oshima (2014) reported that aspirin or acetylsalicylic acid (ASA) is used to treat trauma, infections, and rheumatic diseases. Hagiwara et al. (2014) stated that,” a dose of ASA of greater than 150 mg/kg is toxic, and ASA intake of more than 500 mg/kg causes severe toxicosis” (p. 72). Since an overdose of ASA could be fatal, it is important that companies list the exact amount of aspirin in one tablet. The purpose of this lab is to confirm that aspirin tablets contain the amount of medicine that is advertised on the bottle. If the aspirin bottle states that there is 325 mg in one tablet, then there should be 325 mg of aspirin found when titrated. In an acid base reaction, both solutions are neutralized when there are equal parts of acid and base. This relationship is vital to determine the concentration of a solution through standardization. (Northern Virginia Community College, 2016, para. 1). Solutions are standardized by using titration, which is a method of measuring the volume of a solution needed to fully react and neutralize another reagent (Northern Virginia Community College, 2016, para. 1). To know when the solutions are equivalent, an indicator called phenolphthalein is put into the solution with
In an esterification reaction, a carboxylic acid reacts with an alcohol. The synthesis of aspirin is an esterification reaction. Initially, the proton, i.e. the hydrogen ion, from the acid attacks the acetic anhydride and attaches itself on a double bond oxygen. This makes the compound more electrophilic, meaning that it has a higher affinity for electrons. This is what sets off the reaction. The salicylic acid then acts as an alcohol and attaches its OH group onto a carbon on the acetic anhydride. Then, the hydrogen from the OH group (the alcohol group) of the salicylic acid falls off, forming a tetrahedral intermediate, and the hydrogen ion reassociates with the conjugate base of the acid used as the catalyst. Next, the hydrogen that came from the acid initially, transfers its electrons and forms a double between the adjacent oxygen and carbon. However, the hydrogen atom does not fall off after the transfer of electrons but is kept there with a positive charge. With this, another transfer of electrons occurs and an acetyl group is generated from the breaking of the acetic anhydride. Now, the acetyl group breaks off the positive hydrogen attached and acetic acid is generated as a result. With this, the ester, the aspirin, is created (Watson
Although paracetamol was used clinically for the first time by Joseph von Mering in 1883 and it has been commercialized since 1953, its mechanism has not been discovered yet. However, paracetamol is the most used drug to fight fever and pain currently due to its antipyretic and analgesic properties. The aim of the experiment is the production of paracetamol by formation of an amide bound between the amine group of p-aminophenol and the carbonyl group of acetic anhydride. Furthermore, drugs used in humans must pass Quality Control (QC) and Quality Assurance (QA) in order to ensure the purity of the substance. In the current experiment, methods such as melting point range analysis, Thin Layer Chromatography (TLC) and NMR spectrometry will be used in order to assess the purity level of the synthetized paracetamol.
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.