Synthesis of P-Hydroxy Acetanilide (Paracetamol) Kirstie Leckie B00266969
Abstract
In this experiment the aim was to obtain a pure sample of paracetamol by reduction of p-aminophenol with acetic anhydride. The process carried out to obtain the paracetamol included mixing p-aminophenol, the starting product, with acetic anhydride suspended in distilled water until a precipitate formed (the product). The product was filtered, dried and recrystallized to purify. Infra red spectra for the starting product and the recrystallized and dried product were obtained and compared, and a TLC was run comparing the starting and finishing material. The melting point range of the final product was measured and compared to the literature melting point.
Introduction
P-Hydroxy acetanilide (paracetamol), molecular formula C8H9NO2, is a painkilling drug (analgesic).
It works as a painkiller by inhibiting pain pathways in the central nervous system and in turn dampens the body’s natural pain response. Paracetamol is also fever reducing (antipyretic) and has a relatively low risk of side-effects when taken in recommended doses - it is however potentially toxic in large doses and can lead to acute liver failure (. For it’s antipyretic and analgesic properties, paracetamol is a widely used over the counter medicine for treatment of minor aches and pains, as well as to reduce fevers (Prescott, 2001).
Paracetamol was first synthesised in 1873 by Harmon Northrop Morse by reducing p-aminophenol
Anne is currently taking paracetamol for the pain in her wrist, within healthcare analgesia should always be monitored to assess whether it is achieving elimination of pain and should be adapted to the individual patient (Vargas-Schaffer, 2010). If paracetamol were not effective in eliminating Anne’s pain then practitioners should consider a non-steroidal anti-inflammatory medication [NSAIDS] or a mild opioid medication such as codeine as the next step (Vargas-Schaffer, 2010). However as Anne is asthmatic NSAID medication should be used with caution due to the risk of increased frequency of asthma attacks and breathlessness (Joint Formulary Committee, 2015); if Anne has taken NSAIDS before with no issue then this would be the next choice of analgesia followed by codeine if combined paracetamol and NSAID did not prove effective (Vargas-Schaffer,
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 sodium hydroxide acts to pull the hydrogen off the oxygen in the 2-methylphenol so that the oxygen has a negative charge and can attack the sodium chloroacetate. Again, using a 1:1 molar ratio, 0.34 g (2.9 mmol) of sodium chloroacetate (the good leaving group) was added to 1 ml of water and dissolved. Following dissolving all of the 2-methylphenol (to avoid the sodium hydroxide reacting concurrently with the sodium chloroacetate and 2-methylphenol) in the sodium hydroxide, the aqueous solution of sodium chloroacetate was transferred to the reaction flask. This mixture was then heated to reflux, using a medicine dropper affixed to the top of the flask as an alternative method to boil without
0.1 gram of commercial aspirin was weighed in a tray and was then added to a second test tube containing 2.0 mL of Iron (III) chloride, which was measured using a 10 mL graduated cylinder, to test for phenols. This was repeated once more to validate results.
Addiction to these can happen if taken over a long period of time. Also, irritation of the stomach, liver damage and sleep disturbances as some
Condensation reaction is a chemical reaction that joins two reactants to form a larger molecule with the loss of a small molecule, usually water. 1 This reaction is used as a basis for many important process in the plastic/food industry. The most common being the formation of ester, also known as esterification. When a carboxylic acid is reacted with alcohol in the presence of a dehydrating agent, ester and water molecule are formed as products:
This was concluded by combining information on melting points and TLC; melting range narrowed when filtered product was mixed with the standard product. Also, the Rf value of the pure product is closely related to the Rf value of the standard. TLC of filtrate showed no movement of the substance in the mixture under 9:1 ratio declaring the substance to be extremely polar. Of the three potential unknown reactants, 4-methoxyphenol would be the most polar and therefore would travel least up the TLC plate. (Q14:Yield) 81.2% product yield was collected. “Matter cannot be created nor destroyed”, therefore some product could have filtered through. TLC of filtrate confirmed remnants of product present. Filtering the filtrate could have increased the yield. (Q15:Recovery) The percent recovery of the product makes sense because it is the mass of the crystallized product divided by the crude product: 94.9%. The percentage reflects the mass of pure product (without the presence of impurities). (Q16:MP) Melting point coincides with the unknown nucleophile being 4-methoxyphenol because when the standard product was combined with our pure product, the melting range narrowed. When compared to the melting ranges obtained when mixed with the other two possible products the melting ranges significantly decreased and widened. This is often an indication of impurities being present, but because this was a
In this experiment, 0.31 g (2.87 mmol) of 2-methylphenol was suspended in a 10 mL Erlenmeyer flask along with 1 mL of water and a stir bar. The flask was clamped onto a hotplate/stirrer and turned on so that the stir bar would turn freely. Based on the amount of 2-methylphenol, 0.957 mL (0.00287 mmol) NaOH was calculated and collected in a syringe. The NaOH was then added to the 2-methylphenol solution and allowed to mix completely. In another 10 mL Erlenmeyer flask, 0.34 g (2.92 mmol) of sodium chloroacetate was calculated based on the amount of 2-methylphenol and placed into the flask along with 1 mL of water. The sodium chloroacetate solution was mixed until dissolved. The sodium chloroacetate solution was poured into the 2-methylphenol and NaOH solution after it was fully dissolved using a microscale funnel.
With out all the negative points and side effects to Nyquil, this product does have its advantages. It is one of the best selling products on the market today that relieve minor aches, pains, headaches, muscular aches, sore throat pain, fever, nasal congestion, runny nose and sneezing, and cough due to minor throat and bronchial irritation. Liquid caps or liquid medication are available to take. Nyquil is a wonderful product that works miracles when it comes to cold and flu relief.
The objective of this lab is to synthesize acetaminophen from p-aminophenol. The techniques used to do so, consist of: reflux with heat to allow reaction to occur at a reasonable time period, extraction and filtration to isolate the desired product, and characterization of the product by analyzing IR spectras and melting points. Acetaminophen considered synthesized, primarily due to the IR spectrum exhibiting all the bond vibrations is the amide group. The percent yield of 124.6% imply that there was a mechanical error that occurred, thus, also tampering with the progression of the chemical reaction. The wide melting point range of 165 C-169 C denote the impurity of the acetaminophen product.
AIM: To extract codeine and paracetamol from its tablet by solvent extraction and tentatively identify in comparison to standards using Thin Layer Chromatography.
An ice bath was prepared in a large beaker and a small cotton ball was obtained. 0.5 g of acetanilide, 0.9 g of NaBr, 3mL of ethanol and 2.5 mL acetic acid was measured and gathered into 50mL beakers. In a fume hood, the measured amounts of acetanilide, NaBr, ethanol and acetic acid were mixed in a 25mL Erlenmeyer flask with a stir bar. The flask was plugged with the cotton ball and placed in an ice bath on top of a stir plate. The stir feature was turned on a medium speed. 7mL of bleach was obtained and was slowly added to the stirring flask in the ice bath. Once all the bleach was added, stirring continued for another 2 minutes and then the flask was removed from the ice bath and left to warm up to room temperature. 0.8mL of saturated sodium thiosulfate solution and 0.5mL of NaOH solution were collected in small beakers. The two solutions were added to the flask at room temperature. The flask was gently stirred. Vacuum filtration was used to remove the crude product. The product was weighed and a melting point was taken. The crude product was placed into a clean 25mL Erlenmeyer flask. A large beaker with 50/50 ethanol/water
After all additional product ceased to form, the reaction mixture was cooled in an ice bath to allow precipitation of benzopinacol. The final product was then filtered off from the solution using a Buchener funnel. Its melting point, yield and infrared spetrum was then obtained.
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.
Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene,