Experiment 6A: Williamson Ether Synthesis of Phenacetin This lab synthesized the organic compound phenacetin by performing a Williamson Ether Synthesis on acetaminophen. In this reaction acetaminophen’s hydroxyl hydrogen is substituted for an ethyl group to make phenacetin. An alcohol is being turned into an ester; where, the hydrogen of the hydroxyl group is removed by a carbonate anion and the remaining phenoxide anion backside attacks an ethyl iodine to obtain an ethyl group. If the reaction is successful the melting point should be around 134˙C and the IR spectrum should not have a peak around 3400 cm-1 (hydroxyl bond). To begin the experiment methyl ethyl ketone (solvent) is added to a vial containing the reagents of the reaction: acetaminophen, ethyl iodine, and potassium carbonate. This vial was …show more content…
Since, the extraction is on a microscale the aqueous layer is discarded by using a Pasteur pipette (DCM is denser than water so the aqueous layer is on the top). The organic layer contains the phenacetin (nonpolar) and the aqueous phase contains any remaining acetaminophen (polar). The DCM in the organic layer is then boiled off to reveal the crude product and then the crude product is weighed. The crude product came out to weigh 169 mg compared to the expected 177.79 mg, giving a percent yield of 95.1%. This crude product was then recrystallized to obtain a purer product. The crude product is dissolved in a minimal amount of boiling water (around 4 mL) and then slowly cooled to induce crystallization. After crystals formed (in ice bath) they were vacuum filtered and washed twice with 1 mL of cold deionized water and set to dry. The pure crystals weighed to be 70 mg, giving a percent yield of 39.4%. The dramatic change of product amount from crude to pure was most likely due to procedural error or the fact impurities were present in the
Discussion The third experiment of the semester involves identifying an unknown component of Panacetin, a common pain relief medication, separated and precipitated in the previous experiment. Although Panacetin’s label reports this third ingredient as Tylenol, there is controversy over the true classification of the third substance. This Panacetin label also reports that the unknown constituent makes up 50% of the composition of Panacetin, compared to aspirin’s 40% composition and sucrose’s 10% composition, meaning that it is currently unknown what half of the drug people ingest is identified as. Research results have failed to repeatedly show that the third component of Panacetin is Tylenol, which leads to the hypothesis
The next day an orange goopy textured product resulted. The extracts were then dried and combined with anhydrous sodium sulfate, then evaporated with dry air under the hood in a warm water bath. The liquid was cooled and had an initial weighing of 0.5887g. It was reweighed several minutes later with a final
The phenacetin product collected from the Williamson Ether synthesis (Product A) had an average melting point of 132.0 ˚C -133.5 ˚C, while Amide Synthesis product (Product B) had an average melting of 120.0 ˚C -124.5 ˚C. The MP of a pure substance usually has a range 1-2 ˚C and no significant MP depression. As noted from the data, Product B had a quiet significant depression of 10 ˚C and a range of 5 ˚C, while Product A had a range of 1 ˚C; comparing the melting point data of both products, it can be concluded that Product A has a higher purity. As evident from the data collected from Melting Point analysis, it is highly probable that the product B was contaminated by foreign products.
The product was placed in a Craig tube and several drops of hot (100°C) solvent (50% water, 50% methanol, by volume) was added and heated until all of the crystals dissolved. The Craig tube was plugged and set in an Erlenmeyer flask to cool. Crystallization was induced once the mixture was at room temperature by scratching the inner wall of the tube. It was then placed into an ice bath for ten minutes until crystallization was complete. The tube was then
The problem proposed in the experiment is an unknown ingredient found in generic Panacetin tablets that must be discovered. Panacetin tablets are known to contain aspirin, acetaminophen, and sucrose; therefore, the tablets tested, containing aspirin and sucrose, are thought to contain an unknown of something similar to that of acetaminophen such as acetanilide or phenacetin. Another problem trying to be sought out in the experiments is whether or not the composition of Panacetin as stated on the label is accurate.
349mg of solid acetaminophen was weighed and placed into a 5mL conical vial with a triangular spin vane, point facing downward. Next, 2.6mL of 1M NaOH were added to the same vial. An air condenser was attached to the vial; both were clamped to a stability rod above a hot plate. An aluminum block was placed onto the hot plate stabilize the vial. A small thermometer was placed in the same aluminum block. The solution was heated gently and simultaneously stirred for 10 minutes until all solid was dissolved in the solution. The conical vial was removed from heat set aside to cool. Next, 0.3mL Ethyl iodide was added through the top of the condenser using a Pasteur pipet. The solution was once again heated but this time using the reflux technique.
After production of product 11 hydrogenation of this product can be preformed in H2O with tartaric acid to produce 12. Then the hydroxyl group in 12 can be protected as an ethyl carbonate to produce 13. After this a Grignard addition is used to produce either 16 or 17, with 6 equivalents of Grignard reagent or 10 equivalents (12). Both 16 and 17 can then be pushed towards buprenorphine by treatment with NaOH in methanol/dichloromethane. The best yield pathways are the 11, 12, and 13 pathways with 11 and 12 being easier to conduct, because of the crystalline intermediates
Cold deionized water (20 mL, 1.11 moles) was added into the detached round bottom flask, and the reaction was allowed to crystallize for 2 minutes. The crude product was vacuum filtered, and washed twice with deionized water (50 mL). The filtered crystals were dissolved in ethanol (15 mL, 0.261 moles) in a
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 guaiacol is extracted using diethyl ether from the pills. The solvent is distilled away and the guaiacol is dissolved in methanol in order to be analysed.
This research is important to provide a better understanding for the enhancement of acetaminophen and thiourea because currently there is no concrete evidence that shows the formation of the respective co-crystals. Thus, by exploring this formation by using the three selected techniques which are solvent drop grinding, rotavap, and slow cooling, the interaction between them can be investigated.
Obtain 4 small test tubes and label them while, placing them in a test tube rack.
Equipment, Materials, and Method The equipment used were a jacketed batch reactor beaker, cooling water circulation system, computer, LabPro temperature probe and conductivity probe, mixing stand and magnetic stir bar. The materials used for this reaction were a 0.08M NaOH solution and a 0.1M ethyl acetate solution. A 20% excess Ethyl acetate was used to ensure NaOH was the limiting reactant.[1] NaOH was chosen for the limiting reactant because of its high conductivity relative to Ethyl acetate. The extent of the reaction was monitored by measuring the conductivity throughout the reaction. With NaOH being the limiting reactant, the change in conductivity is more visible, and the termination of the reaction can
There are three purpose of this lab, the first purpose is to observe limiting reactant and excess reactant in a chemical reaction. Second purpose is to observe and determine the percent yield. And the third purpose of this lab is to combine two aqueous ionic solutions to form an insoluble precipitate commonly referred to as chalk.
Lastly, add an additional of cold water to the mixture and collect crude products by suction filtration. 2, we need to dissolve crude product in ethanol. Secondly, add hot distilled water to it and allow it to cool. Lastly, perform suction filtration, put crystal on watch glass, put into oven then desiccator. And Crystal will be obtained in the end of the experiment.