However, if you recovered at least 3. This is the combination of the salicylic acid and acetic anhydride thus forming the Aspirin also known as the Acetylsalicyc lic Acid. Synthesis of Salicylic Acid from Wintergreen Oil Synthesis of Salicylic Acid from Wintergreen Oil Objective — Preparation of salicylic acid organic synthesis from methyl salicylate utilizing previously used procedure from the nineteenth century. Wintergreen oil which is at least 98% methyl salicylate can be found for a good price in many drugstores. The sample became a cloudy white color.
Hydrolysis of Methyl Salicylate and Synthesis of Acetylsalicylic Acid Objectives Many naturally occurring chemicals can be used isolated and used to make other compounds. What size and kind of glassware do you need? The reaction for synthesis of acetylsalicylic acid is shown in the following figure. When choosing consider: the mechanism Starting Materials 3. Choosing a solvent - characteristics of a good one 2. One of the esters, acetylsalicylic acid, is aspirin, the common analgesic. This process allowed for the successful production of 1.
The type of reaction may be known as condensation reaction because the small molecule of H 2O is eliminated from the reactants while the remaining bits of the reactants condense together to give the main product. A boiling stone was then dropped to the bottom of the round bottom flask. Second, we will perform a hydrolysis reaction. Introduction The carbon-carbon double bond of alkenes represents a site that has a high electron intensity. At this point, remove from heat, and feel the edges of the container. Acetic anhydride will be used in this experiment so that when ester is formed, water is not produced. Hydrolysis occurs when water is used to break a bond.
In a previous experiment, we have used the Fischer esterification reaction to produce isopentyl acetate from an acid acetic acid and an alcohol isopentyl alcohol. The mixture will be acidic, but too much acid will not be a problem: Acid stays acid in acid! Methyl salicylate was first isolated in pure form in 1843 by extraction from wintergreen plant Gaultheria. Filter the solution through one or two coffee filters, squeezing the filters into the filtrate afterward to recover some of the liquid. Sodium salicylate, a predecessor to aspirin, was developed along with salicylic acid in 1875 as a pain reliever. On performing the FeCl3 test, the collected products were now separated in each test tube.
In this experiment the experimenters will prepare two esters of o-hydroxybenzoic acid, more commonly known as salicylic acid. Somehow need molecules to collide to get over activation barriers to form product heating is required. This method effectively washes the crystals and lets the contaminants get diluted into the solvent. The solution was put on the hot plate till the solid dissolved and was immediately taken off. Mass of Salicylic Acid 0. Loss of product occurred due to loss at each transfer step including, crystals stuck to the vacuum filter, crystals sticking to the glass stir rod for pH testing as well as the metal spatula used for recrystallization. The general theory behind this experiment was to study the synthesis of a drug from organic materials.
Candles can also be made from beeswax, soy, other plant waxes, and tallow a by-product of beef-fat rendering. This site is susceptible to oxidation. The amount of product formed is limited by this reagent because the reaction cannot proceed further without it. When it is about room temperature the beaker will feel slightly cool to the touch , place the beaker in an ice bucket to continue to produce crystals. Both extraction and distillation were employed to obtain a pure product.
The sample was allowed to dry for a few minutes and then weighed. Hydrolysis can occur in either basic or acidic conditions. The flask and its contents were allowed to sit at room temperature while crystallization occurred. Oil is and will continue to be an important resource that people directly and indirectly use nearly everyday. The ice bath kept the temperature low enough that the salicylic acid remained solid and the sulfuric acid components liquid, allowing for a final product with the most purity possible.
Then, phosphoric acid would catalyze the reaction and water would be added to decompose the remaining acetic anhydride. The mixture was heated for about 15 minutes as the white solid dissolved. Which gives only indirect evidence? The earliest known uses of the drug can be traced back to the Greek physician Hippocrates in the fifth century B. This reaction produces disodium salicylic acid, methyl hydroxide and water molecules. So, if the solid is not freely flowing in the beaker, add enough water so that the solid is suspended and a liquid slurry appearance. Aim: To prepare methyl salicylate from salicylic acid.
It is sometimes used to treat or prevent heart attacks, strokes, and angina. The advantage of using acetic anhydride is that you do not produce water which can be used for hydrolysis of the newly formed ester. The aspirin was dissolved first with 5 mL of distilled water. After you are done refluxing and the contents of your beaker have cooled to room temperature, fill the remainder of the beaker with very cold ice water. In order… Acetylsalicylic Acid from Salicylic Acid Shultz, Joshua T. The weight was found to be. On contrary, the melting point of the aspirin is 130 It can be hypothesize that the Aspirin made is a successful one.
Caution: Aspirin decomposes in boiling water therefore, do not boil the aspirin or when dissolved in solutions of alkali hydroxides and carbonates. A clamp was used to hold the apparatus steady and hold fast to a vertical rod in the hood. While both product compounds in the experiment are esters of the same compound salicylic acid , they are quite different in structure. This was an acid catalyzed Fischer esterification. Amount of methyl salicylate used: 1???? Assignment 2: The peak located at 8. Why is it that dilute sulfuric acid does not allow the reaction to proceed while concentrated sulfuric acid does? The equilibrium of the reaction was changed by adding an excess amount of acetic acid. Do a yield, percent yield, and melt temp of your re-crystallized aspirin.