This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. Synthesis of salicylic acid from wintergreen oil essay. Put a few small chips of porous porcelain, set a reflux condenser to the flask and boil the mixture gently for 5 h. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone.
Show full abstract salicylic acid, obtained via hydrolysis of the methyl salicylate, was converted to aspirin using soft drinks or fruit juices as catalysts in a microwave synthesis. Place the test tube in the hood in a water bath at 70 c for 15 minutes. 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 gaultheria procumbens is one of the species with the highest concentration of this compound, and therefore this molecule is known as gaultheria essential oil. Kaitlin saloky purpose the purpose of this lab was to convert acetylsalicylic acid to methyl salicylate while monitoring the reaction progress using tlc. When salicylic acid combines with methanol it becomes the ester known as methyl salicylate or oil of wintergreen. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of betula lenta sweet birch and gaultheria procumbens eastern teaberry or wintergreen. The two different functional groups on the aromatic ring are utilized in this lab. This syntheses is to convert the salicylic acid into methyl salicylate via the fischer esterification reaction.
In this lab you will you will hydrolyze methyl salicylate to salicylic acidafford and methanol, as shown below in scheme 1. Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. The salicylic acid is a solid that can be isolated and purified by crystallization. Salicylic acid from latin salix, willow tree is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. First, the free carboxylic acid group will be produced when we hydrolyze the methyl salicylate. Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen. Methyl salicylate can be produced by esterifying salicylic acid with methanol.
The experiment was carried out using a reflux condenser under heat because heat is needed to increase the rate of the reaction and the reflux condenser insures that none of the product is boiled away. It can be used as an additive in food, because it has a flavor similar to mint. Methanol is also known as methyl alcohol and wood alcohol. Methanol is the alcohol which is released by hydrolysis. Synthesis of oil of wintergreen cornell center for. Sodium salicylate is reacted with sulfuric acid or hydrochloric acid to remove the sodium ion and forms salicylic acid with sodium sulphate as a byproduct. The acid reacts with methanol under acidic conditions aq. Lab a synthesis of salicylic acid flashcards quizlet. Salicylic acid to methyl salicylate part three youtube. Distil off the excess amount of alcohol on a water bath and allow. Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. Our starting material is aspirin acetylsalicylic acid. Methyl salicylate, or wintergreen oil, is an organic ester naturally produced by the wintergreen plant group, and commonly made by the esterfication of salicylic acid with methanol. This hydrolysis is catalyzed by base in this case naoh, and therefore the initial product of the reaction is the sodium salt of salicylic acid.
Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. Discussion in this synthesis, methyl salicylate is the starting material or precursor and salicylic. Sp11 1021 synthesis of aspirin and oil of wintergreen. Methyl salicylate is an organic compound with the formula c6h4ohco2ch3. Methyl salicylate naturally found in the bark of sweet birch tree betula lenta round bottom flask condenser 2 rubber tubings separatory funnel vials bunsen burner tripod water bath clamps iron stand slowly add small portions of 20% sodium carbonate solution with constant.
Synthesis of salicylic acid from wintergreen oil essay 996. Methyl salicylate is an ester salicylic acid derivative found in many plants. Methyl salicylate is a liquid compound with a minty smell that is used to flavor candy and perfumes methyl salicylate is also one of the active ingredients along with menthol in the bengay painrelieving ointment a simple change in the functional group from a methyl ester to a carboxylic acid turns methyl salicylate into salicylic acid. Other articles where methyl salicylate is discussed. Methyl salicylate an ester can be hydrolyzed to produce salicylic acid. Olatunji department of chemistry, university of ilorin, pmb 1515, ilorin, nigeria.
The purpose of this experiment is to take methyl salicylate wintergreen oil and by heating it under reflux with naoh as a solvent, and then cooling the mixture with h2so4 as another solvent, synthesize salicylic acid. Methyl salicylate an overview sciencedirect topics. What is the product of methanol and salicylic acid. Methyl salicylate is an ester and esters are formed from a carboxylic acid and an alcohol. Methyl salicylate is used as a rubefacient in topical analgesics, in low concentrations as a flavoring agent in chewing gum, and in chemical warfare research. Carefully add 20 drops of concentrated sulfuric acid h2so4 to the test tube. Cn102267911a synthesis method of methyl salicylate. Salicylic acid is ortho hydroxy benzoic acid which undergoes esterification with methanol to form methyl salicylate, having a specific smell of iodex, in presence of concentrated h2so4 to remove water. When methyl salicylate is prepared from salicylic acid and methanol, an oh is the leaving group from the salicylic acid. Synthesis of salicylic acid from alkyl salicylate labmonk.
Aqueous h2so4 is the catalyst driving the reaction to its equilibrium. The reaction of salicylic acid c 6 h 4 ohco 2 h and methanol ch 3 oh forms this ester. Methyl salicylate, or wintergreen oil, is an organic ester. Molar mass methyl salicylate 152 gmole moles methyl salicylate present 2. It has a role as a flavouring agent, a metabolite and an insect attractant. Add 10ml of methanol to the test tube and gently shake the test tube until all of the salicylic acid has dissolved. The purpose of this lab was to get students familiar with glass materials often used by organic chemists and how to reflux a mixture and to filter its precipitate, through teaching students how to create salicylic acid from methyl salicylate. As a derivative of salicylic acid, it is used commonly in ointments for the relief of muscle. Esters react with acids to liberate heat along with alcohols and acids. What is the purpose of adding concentrated sulfuric acid in the preparation of methyl salicylate. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an ec 1. Gaultheria procumbens cahours identifie methyl salicylate as. Methyl salicylate appears as colorless yellowish or. Mar 27, 2014 synthesis of salicylic acid from wintergreen oil by.
The experiment was carried out to describe the s y nthesis of salicylic acid using meth yl salicylate wintergreen oil. Green 3 step synthesis of methyl salicylate sophia. The preparation of methyl benzoate and methyl salicylate. Experiment 22 synthesis of aspirin and oil of wintergreen. Synthesis of salicylic acid from wintergreen oil abstract. Methyl salicylate may be used by plants as a pheromone to warn other plants of.
Stir the mixture until the salicylic acid dissolves. To synthesize methyl salicylate by esterification of acetylsalicylic with methanol. An investigation of the acid catalyzed esterification of benzoic acid and salicylic acid with methanol on. Necessary reagents methanol, ch 3oh salicylic acid, ohc 6h 4cooh concentrated sulfuric acid, h 2so 4 outline of procedure. Case study for the synthesis of methyl salicylate studocu. In methyl salicylate oil of wintergreen, the cooh group of salicylic acid is esterified with methanol ch3oh, whereas in acetylsalicylic acid. Since it breaks down into salicylic acid and methanol, small amounts can be poured down the drain. In methyl salicylate oil of wintergreen, the cooh group of salicylic acid is esterified with methanol ch3oh, whereas in acetylsalicylic acid aspirin the acid component of the ester is acetic acid, and salicylic acid contributes the phenolic. In its pure form, methyl salicylate is highly toxic as. Preparation of methyl salicylate, by sciencemadness. When methanol is heated with salicylic acid in presence of conc. Examples include drugs, synthetic fabrics, paints, plastics, etc. Jun 07, 2017 here we prepare some methyl salicylate from salicylic acid and methanol.
The invention relates to a synthesis method of methyl salicylate, and the synthesis method comprises the following reaction steps. What is the chemical formula for the product of salicylic. Here we prepare some methyl salicylate from salicylic acid and methanol. Methyl salicylate oil of wintergreen is an organic ester. Heat is also generated by the interaction of esters with caustic solutions. Heres a simple synthesis of methyl salicylate oil of wintergreen, for those that just started organic chemistry though of course, even if you are a bit more experienced, nothing beats a minty smelling. A student completed the synthesis of salicyclic acid just. The reaction begins with a transesterification to yield salicylic acid. Methyl salicylate can be safely burned, either alone or mixed with a more flammable and volatile solvent, like ethanol.
Weigh approximately 1g of salicylic acid and place in a test tube. Synthesis of salicylic acid from wintergreen oil purpose. Synthesis of oil of wintergreen cornell center for materials. In addition to serving as an important active metabolite of aspirin. Methyl salicylate is a liquid compound with a minty smell that is used to flavor candy and perfumesmethyl salicylate is also one of the active ingredients along with menthol in the bengay painrelieving ointment a simple change in the functional group from a methyl ester to a carboxylic acid turns methyl salicylate into salicylic acid. The purpose of this lab was to get students familiar with glass materials often used by organic chemists and how to reflux a mixture and to filter its precipitate, through teaching students how to create salicylic acid from methyl salicylate wintergreen oil. Methyl salicylate is used as a rubefacient in topical analgesics, in low. A student completed the synthesis of salicyclic acid just as we did in our laboratory activity. Methyl salicylate synthesis summer 2016 background. Here one mole of methyl salicylate oil of wintergreen reacts with two moles of sodium hydroxide to form sodium salicylate with methanol and water, each of one mole. Preparation of oil of wintergreen from commercial aspirin tablets. What is the chemical equation for methyl salicylate answers. Synthesis of oil of wintergreen pre lab discussion. It is a benzoate ester and a member of salicylates.
This reaction will connect the salicylic acid to the methanol with. It is easier to prepare is from salicylic acid by refuxing in methanol in the presence of an acid like ptsoh or sulfuric acid. A student completed the synthesis of salicyclic acid just as. Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. Sulfuric acid is used in esterfication reactions as a catalyst. The chemical equations that describe this experiment are. The type of reaction may be known as condensation reaction because the small molecule of h 2 o is eliminated from the reactants while the remaining bits of the reactants condense together to give the main product. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. When salicylic acid reacts with methanol in the presence of an acid catalyst, methyl salicylate, or oil of wintergreen, is produced according to the following equation. The preparation of methyl benzoate and methyl salicylate on silica gel column o. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Salicylates, including salicylic acid sa, methyl salicylate, saligenin and their respective glucosides, are natural products of plant metabolism that have long been known to possess therapeutic properties.
Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. Place the conical vial in an aluminum block on a stirring hotplate, and, while stirring, slowly, and in small portions, add 0. Recrystallization of salicylic acid lab recrystallization of salicylic acid lab. When salicylic acid reacts with methanol, methyl salicylate commonly known as oil of wintergreen is formed. The final product will then be evaluated in comparison to salicylic acid made from benzene. It is obtained from the bark of the white willow and wintergreen leaves. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. H2so4 is therefore neither reacted nor formed in this reaction. Interestingly, methyl salicylate and methyl benzoate are both produced by methylation of salicylic and benzoic acids, respectively, controlled by the same gene in a. The chemical formula of methyl salicylate is c6h4ohcooch3, it can also be written. Find patient medical information for salicylic acidmethyl salicylatetalc topical on webmd including its uses, side effects and safety, interactions, pictures, warnings and user ratings. Discussion the methyl salicylate is formed through a combination of transesterification and a fischer esterification mechanism, which involves the intermediate salicylic.
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