Green synthesis of methyl salicylate using novel sulfated. Synthesis, characterization and antimicrobial studies of salicylic acid complexes of some. An investigation of the acid catalyzed esterification of benzoic acid and salicylic acid with methanol on silica gel solid support system was carried out. Synthesis of the deoterospecific 4d and 6d methyl 3, 5. Chemical ecology, pheromones, pheromone, moth, moths, insect, sex, attractants, attractant, sexattractants, insects, entomology, behaviour, behavior, lepidoptera. The maximum allowable amount of free salicylic acid in an aspirin sample is 0. Salicylic acid is a milder and safer treatment for mild to moderate acne vulgaris, with fewer side effects. Synthesis of oil of wintergreen cornell center for. Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. Synthesis of methyl salicylate over mesoporous aluminosilicate. The synthesis of methyl salicylate is a safe and effective way to observe an amine diazotization. Pdf this paper presents a multidrug fatality in which methyl salicylate was ingested. Jsci has precedent for use at a maximum concentration of 0.
Philadelphia collegeof pharmacy and science, philadelphia, pa. Synthesis, characterization and antimicrobial studies of. An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been replaced by and alkoxy oalkyl group. Aspirin involves a reaction of the oh group of salicylic acid, while methyl salicylate involves a reaction of the.
General methyl salicylate from oil of wintergreen, and salicylic acid from latin salix, willow tree are both natural products. The toxicity and metabolism of methyl salicylate were investigated in the belief that it functions primarily as its hydrolytic product, free salicylate. An ester compromises an organic or inorganic acid in which one or more hydroxy. Oacetylation of salicylic acid to give acetylsalicylate aspirin. This reaction is the reverse of the synthesis reaction. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. An ester is a compound that is formed when an acid containing the.
In salicylic acid of an acid catalyst gives methyl salicylate, synthetic oil of wintergreen, which is used as a flavouring agent. It has a role as a flavouring agent, a metabolite and an insect attractant. Yields of salicylic acid week 1 and ethyl salicylate will be found, as well as the overall yield of the 2step conversion of acetyl salicylic acid to ethyl salicylate. View lab report synthesis of methyl salicylate lab report.
Salicylic acid from latin salix, willow tree is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid bha. The esters produced in this laboratory experiment contain what functional group characteristic of all ester. Salicylic acid is a key ingredient in many skincare products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It is a benzoate ester and a member of salicylates. This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. 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. Journal of chemical education, v65 n12 p1106 dec 1988. Synthesizing aspirin and oil of wintergreen purpose in this experiment, you will synthesize acetylsalicylic acid, commonly known as aspirin, and methyl salicylate, oil of wintergreen, from salicylic acid. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Synthesis of aspirin and oil of wintergreen revision f8 page 2 of 7 methyl salicylate is the active ingredient in oil of wintergreen.
Plasma analyses for methyl salicylate and free salicylate after oral administration of the ester to rats and dogs demonstrate complete hydrolysis shortly after. Leeet at activation of the ba2h activity resulted in a significant increase in salevels in hydrogen peroxidetreated tobacco leaves j. In this experiment, you will measure the melting point of your synthesized asa product, salicylic acid, a crushed aspirin tablet, and pure asa from a manufacturer. Request pdf synthesis of methyl salicylate over mesoporous aluminosilicate materials different from the traditional synthesis of methyl salicylate, the. The two compounds we will be preparing, aspirin acetylsalicylic acid and oil of wintergreen methyl salicylate, are both organic esters. When an acid containing the cooh group reacts with an alcohol a compound containing an oh group formed an ester. Structurally, methyl salicylate is the methyl ester of salicylic acid, produced e. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of salicylic. Methyl salicylate and salicylic acid were detected using an extraction solution of acetonitrile coupled with internal standard and then analyzed by hplcdiodearray detection. Salicylic acid can be prepared by heating methyl salicylate with water.
Molecular formula of methyl salicylate c 8 h 8 o 3. Designing a bacterium that will generate an enzyme for a pathway to produce salicylic acid would be an effective solution that would resolve many complications connected to chemical synthesis of salicylic acid. Methyl salicylate is a naturally occurring compound that we will use to produce salicylic acid, which will then be used to make the wonder drug aspirin acetylsalicylic acid. Methyl salicylate from oil of wintergreen, and salicylic acid from latin salix, willow tree are both natural products. Print student copies for the lab on the synthesis of wintergreen. Because of its concentrated liquid form, methyl salicylate ingestion can cause rapid onset salicylate. Experiment 22 synthesis of aspirin and oil of wintergreen. Analysis of methyl salicylate and salicylic acid from. Synthesis of salicylic acid from wintergreen oil purpose. It also includes pleasant smells due to chemicals that are used for artificial flavorings.
Methyl salicylate c6h4 ho cooch3, also known as salicylic acid methyl ester, oil of wintergreen, is a natural product of many species of plants. Add 4 drops of concentrated sulfuric acid to the mixture and stir. Sigmaaldrich offers a number of methyl salicylate products. Small organic acid molecules such as jasmonic acid and salicylic acid have been shown to form methyl esters in plants. Sp11 1021 synthesis of aspirin and oil of wintergreen. The salicylic acid prepared in this experiment will be the starting material for the preparation of aspirin by our chemistry 1 students. The method involved distilling continuously or refluxing. Synthesis of methyl salicylate from aspirin esters are a class of organic compounds.
Methyl salicylate, for example, is oil of wintergreen, isopentenyl acetate is oil of banana or pear, butyl butanoate smells like pineapple, propyl2methylpropanoate smells like rum and pdimethylterephthalate and ethylene glycol antifreeze are used to make dacron. Salts of organic compounds usually are soluble in water or will dissolve in. This is not the source of salicylic acid in the industrial synthesis of aspirin, but it is, nevertheless, a good one for laboratory use. The reactions were carried out in n,ndimethylformamide dmf in the presence of anhydrous potassium. Olatunji department of chemistry, university of ilorin, pmb 1515, ilorin, nigeria. Request pdf green synthesis of methyl salicylate using novel sulfated iron oxidezirconia catalyst esters of salicylic acid are in demand for the synthesis of drugs, food preservatives. The preparation of methyl benzoate and methyl salicylate on silica gel column o. It has a role as a flavouring agent, a metabolite and an. Methyl salicylate possesses essentially the same ld5o in mice as sodium salicylate. Methyl salicylate synthesis summer 2016 background. Search results for methyl salicylate at sigmaaldrich. Different phenol content ranges seeking one purpose.
This compound, which has a familiar odor is used as a flavoring agent and in rubbing ointments. It works as an exfoliant and mostly acts against comedonal acne by slowing follicular shedding of cells thus preventing clogging. Methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus. Acetic acid and salicylic acid contain what functional group characteristic of all carboxylic acids. The two step synthesis encompasses aqueous base hydrolysis of wintergreen oil methyl salicylate, ms to salicylic acid sa followed by acetylation to acetylsalicylic acid aspirin, asa. Case study for the synthesis of methyl salicylate studocu. Seqens is a main actor in pharmaceutical synthesis and specialty ingredients. The hydrolysis reaction that occurs will form methanol, water, and the sodium salt of salicylic acid. It appears that in lower animals the toxicity of methyl salicylate is essentially identical with that of salicylic. In the event you find this near sunrise filled with anxiety, rage and confusion i hope this gives you a hand. A simple onestep procedure for synthesis of 1methoxy1oxoalkan2yl salicylates and 1methoxy1oxoalkan2yl 21methoxy1oxoalkan2yloxybenzoates by reaction of salicylic acid with several methyl 2bromoalkanoates was developed.
An ester compromises an organic or inorganic acid in which one or more hydroxy oh groups have been. Methyl salicylate oil of wintergreen is an organic ester. Salicylic acid is converted to the liquid ethyl salicylate by addition of ethanol. On the metabolism and toxicity of methyl salicylate journal. Although this reaction has been microscaled, it is. Pdf the analysis of methyl salicylate and salicylic acid from. You will be able to see how two very different organic compounds can be made from the same common starting material. An investigation of the acid catalyzed esterification of benzoic acid and salicylic. The type of reaction may be known as condensation reaction because the small molecule of h2o is eliminated from the reactants while the remaining bits of the. In this lab you will you will hydrolyze methyl salicylate to salicylic acidafford and methanol, as shown below in scheme 1. See the mechanism and discussion in klein on saponification of esters, sections 21. 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.
The major site of hydrolysis of methyl salicylate in the rat, rabbit, dog and monkey is the liver, although intestine, kidney, pancreas, and spleen may play a minor role in such breakdown. Isobutyl alcohol and formic acid combine to produce a raspberry odor. Synthesis of robust electrochemical substrate and fabrication of. In the present study, motivated by important applications, we have focused on the synthesis of methyl 4r salicylate derivatives r c 5 nh 4, c 4 sh 3, c 4 seh 4 and elucidated their unique spectroscopic. Synthesis of the deuterospecific 4d and 6d methyl 3,sdinitrosalicylates. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. Preparation of methyl salicylate, by darkblade48 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. Because of its concentrated liquid form, methyl salicylate ingestion can cause rapid onset salicylate toxicity. The synthesis uses diazonium salts to replace the amine group of an aromatic amine with a hydroxyl group. General methyl salicylate from oil of wintergreen, and salicylic. View lab report synthesis of methyl salicylate from aspirin. Salicylic acid allows cells of the epidermis to more readily slough off. This substance has caused adverse reproductive and fetal effects in animals.
Necessary reagents methanol, ch 3oh salicylic acid, ohc 6h 4cooh. Further down the salicylic acid chain, seqens eds offers a comprehensive portfolio of methyl salicylate grades. This experiment illustrates several properties of organic synthesis. The product will be analyzed by melting point analysis and carbon nmr. Functional analysis of a tomato salicylic acid methyl transferase and its role in synthesis of the. Hydrolysis of methyl salicylate oil of wintergreen to give salicylic acid. Treatment of salicylic acid with phenol gives phenyl salicylate, which is used for sunburn creams and entericcoated pills and to make salicylanilide for use as a fungicide and mildew preventive. Preparation of salicylic acid salicylic acid will be prepared by a basepromoted hydrolysis, or saponi. The plant journal functional analysis of a tomato salicylic.
Methyl salicylate is an ester easily recognized by its odor and is known as oil of wintergreen because of its natural source. The purpose of this experiment was to perform a basecatalyzed hydrolysis reaction while converting oil of wintergreen to salicylic acid. Nsf ccli project page 1 experiment oil of wintergreen. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of root beer. Synthesis and antifungal activity of new salicylic acid. The preparation of methyl benzoate and methyl salicylate. Put 3 grams of salicylic acid and 6 ml of acetic anhydride in a 250 ml erlenmeyer flask. Synthesis of oil of wintergreen pre lab discussion. Preparation of salicylic acid santa monica college. Discover methyl salicylate pharma, a seqens essential drug subtances product.
The c nmr has extra signal compared to that of salicylic. 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. This is not the source of salicylic acid in the industrial synthesis. Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. Analysis of methyl salicylate and salicylic acid from chinese. This procedure will use starting materials that can be found at a. In the presence of moisture, aspirin may decompose hydrolysis into salicylic acid and acetic acid. Methyl salicylate is also used as a bait for attracting male orchid bees for study, which apparently gather the chemical to synthesize pheromones, and to clear plant or animal tissue samples of color, and as. Synthesis of oil of wintergreen cornell center for materials research.
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