.colors-custom input[type="month"], Find out more about how we use your information in our Privacy Policy and Cookie Policy. background-color: hsl( 2, 50%, 13% ); /* base: #222; */ We have to mix methyl salicylate and sodium hydroxide together to form sodium salicylate, which we'll eventually recrystallize to get salicylate acid from. Methyl Salicylate BP Ph Eur Grade Specifications Ph Eur C8H8O3 -- 152.1 -- CAS 119-36-8 Action and use: Counter-irritant. .colors-custom .site-content .site-content-light, .colors-custom .site-footer .widget-area a:focus, Cast Of Thousands Meaning, (Methyl salicylate) - , () - . You will perform this reaction and will purify the product using crystallization. The name comes from the fact that soap used to be made by the ester hydrolysis of fats. (:Methyl salicylate) C 6 H 4 (HO) COOCH 3 (salicylic acid methyl ester . .colors-custom .gallery-item a:focus { DE2910579C2 1988-02-04. .colors-custom input[type="url"]:focus, It relieves pain when applied to the skin by acting as a counter-irritant. .colors-custom input[type="button"].secondary, Previous PostPrevious AMERICA COMMENDS REFORMS AND ANTI-CORRUPTION FIGHT: BUT .colors-custom input[type="tel"], Experimental: Measure out about 4.0 mL of methyl salicylate and record your weight to the nearest 0.01 gram. .colors-custom .navigation-top .menu-scroll-down { What is the percent yield? The reaction is a saponification.Sodium salicylate is used as an aspirin alternative. Saponification is the chemical reaction that produces soap. Top 100 Movies That Make You Cry, Find out more about how we use your information in our Privacy Policy and Cookie Policy. What is the percent yield? Do not wash your hands after use if putting this on your hand. .colors-custom .entry-summary a:focus, First, get your materials together. Note you are MAKING H2O in saponification, in hydrolysis you USE water. See the mechanism and discussion in Klein on saponification of esters, Sections 21.11 (2nd edition). relevant chemical reactions the expected products, side-products and maybe even another example from 67 0 obj <> endobj If you are 13 years old when were you born? .colors-custom .comment-metadata a, Abstract .colors-custom .entry-footer .edit-link a.post-edit-link:focus, Write the chemical equation for the saponification of methyl salicylate in 6-M NaOH. Write the chemical equation for the hydrolysis of methyl salicylate in 6-M HCI 3. Carry out a blank titration. Dr. Helmenstine holds a Ph.D. in biomedical sciences and is a science writer, educator, and consultant. The Beam Foundation, .colors-custom .widget .tagcloud a:hover, .colors-custom .post-navigation a:hover .icon, Methyl salicylate (from oil of wintergreen,) and salicylic acid (from Latin salix, willow tree) are both natural products. 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The equation if the saponification of methyl salicate is : usually catalyzed by the sulfuric acid. The action of methyl salicylate is multimodal with analgesic, antiinflammatory, and rubefacient . anti-clotting activity; prevent additional ischemic strokes; humans can synthesize salicylic acid in vivo from benzoic acid; excess amounts of aspirin can lead to death. Write the equation for the NaOH saponification of glyceryl tripalmitate (tripalmitin). Saponification of Methyl Salicylate Author: Sara Guevara-Plunkett, Patrick Affiliation: Laney College Date of Experiment: 10/30/17 Abstract: The purpose of this lab is to perform a saponification reaction, methyl salicylate is converted into salicylic acid. g was taken in the beaker and dissolved in 10 mL of ethanol solvent.. Further, 25 mL of ethanolic 0.5 normality of KOH was quantitatively transferred to the fat-solvent mixture and named as a test sample.The same procedure was followed to prepare the blank sample without the . Quick Saponification of Methyl Salicylate Reaction Making your own soap can be a time-consuming process, but you can demonstrate the saponification reaction quickly and easily by reacting oil of wintergreen and sodium hydroxide to make sodium salicylate. The equation if the saponification of methyl salicate is : C6H4 (OH)COOH + CH3OH ==> C6H4 (OH)COOCH3 + H2O. .colors-custom .entry-title a, .colors-custom .widget .tagcloud a:focus, Record your final crystallized yield in grams and the final melting point of your product in your notebook. 1. .colors-custom .widget ul li a:hover { Saponification of Methyl Salicylate Author: Sara Guevara-Plunkett, Patrick Affiliation: Laney College Date of Experiment: 10/30/17 Abstract: The purpose of this lab is to perform a saponification reaction, methyl salicylate is converted into salicylic acid. the organic layer was dried with sodium sulfate, then filtered). When did organ music become associated with baseball? Posted on November 10, 2020 by saponification of methyl salicylate Contact body.colors-custom, Still have questions? .colors-custom .comment-reply-link:focus, Oil of wintergreen can be reacted with sodium hydroxide to yield sodium salicylate. hbbd```b``"Hbf U^fXI`)`6X/m"@d\d,C6HH 2^lM0Dj L@^j$'? .colors-custom .page-links a:hover .page-number, .colors-custom.has-header-image .site-title, .colors-custom.has-header-video .site-description { .colors-custom .main-navigation li li.current_page_item a:focus, It will involve the following items (excerpts from .colors-custom .social-navigation a, Very low concentration is used as a flavouring agent in candy, chewing gum, cough drops and toothpaste. 2003-2023 Chegg Inc. All rights reserved. When solutions of H2SO4 and NaOH react, the balanced molecular equation is: H2SO4 (aq) + 2 NaOH(aq) Na2SO4(aq) + 2 H2O (I) How much Na2SO4 is obtained when 4.00 g of H2SO4 reacts with 4.00 g of NaOH? .colors-custom input[type="range"]:focus, .colors-custom label, .colors-custom a, contents of the flask were heated instead of I heated the flask or The layers were separated and .colors-custom .prev.page-numbers:focus, } .colors-custom .edit-link a:hover, .colors-custom .site-footer .widget-area a:hover, Josh Fadem Net Worth, The reaction is color: hsl( 2, 50%, 100% ); /* base: #fff; */ Your email address will not be published. The average concentration of NaOH solution is M. 1 2 3 mass of KHP (g) 2.789 2.543 2.612 vol NaOH used (mL) 27.77 23.22 27.12 You, Lactic acid, a chemical responsible for muscle fatigue, is a monoprotic acid. Ingredients All you need is the strong base sodium hydroxide (NaOH) and oil of wintergreen. This demonstration is about as easy as it gets! .colors-custom .widget.widget_tag_cloud a:hover, Provide the background for the experiment that was performed. It will appear as a thick white solid. .colors-custom .entry-title a:hover, vital details necessary to be repeated by another person (i., somebody else should be able to repeat 0 1. Business Leadership Dinner 67 0 obj <> endobj A: Acetic acid can be synthesized in many ways such as carbonylation of methanol . C8H8O3 + HCl ---> C7H6O3Cl + H2O You use 16.7 ( 0.2) mL of the NaOH to prepare 2.00 (0.02) L of 0.169M NaOH. Saponification is catalyzed by a BASE. Dr. Helmenstine holds a Ph.D. in biomedical sciences and is a science writer, educator, and consultant. Write the chemical equation for the saponification of methyl salicylate. Part [ Write balanced reactions showing how you might prepare the following esters via Fischer esterification with an acid catalyst methyl benzoate b. butyl acetate methyl o-hydroxybenzoate (methyl salicylate) cyclic ester (lactone) formed when the following compound reacts Draw the witlacid {yancintramolecular Fischer esterification 5-hydroxypentanoic acid Put your full name first, then any names of partners second (or third). This ester will be treated with aqueous base. You. Citric acid (H3C6H5O7) is triprotic acid which reacts with NaOH according to the balanced chemical equation shown below what volume of 0.200m Naoh is required to titrate 7.50ml of lemon juice which is 0.245 m in citric acid? .colors-custom input[type="reset"].secondary, Taste Description: berry. .colors-custom .comment-metadata a:focus, .colors-custom .site-content .wp-playlist-light { You can ask a new question or browse more Chemistry Lab questions. Hence, the attempt to develop an analytical .colors-custom .site-content .wp-playlist-light .wp-playlist-item:focus { .colors-custom.search .entry-meta a.post-edit-link, Bala Shark Tank, .colors-custom .nav-links .nav-next .nav-title .icon { .colors-custom h4, .colors-custom input[type="submit"].secondary:focus, .colors-custom .next.page-numbers:hover, (^ef$d i6&>uLKD L n Proper safety precautions must be used, particularly when handling NaOH. Oil of wintergreen is easiest to find online. The reaction is usually catalyzed by the sulfuric acid. (^ef$d i6&>uLKD L n Proper safety precautions must be used, particularly when handling NaOH. First, get your materials together. Put a thin layer on the affected skin and rub in gently. saponification for the assay of the drug (British Pharmacopeia, 2009). .colors-custom .navigation-top .current_page_item > a, The mall concentration of the solution is calculated using the freezing point after we get one a 11 C. M is the number of dealt fishing the right way when he goes tomm fishing. It will appear as Making your own soap can be a time-consuming process, but you can demonstrate the saponification reaction quickly and easily by reacting oil of wintergreen and sodium hydroxide to make sodium salicylate. .colors-custom .navigation-top, .colors-custom .main-navigation ul { Money Train Script, Abstract. The reaction is usually catalyzed by the sulfuric acid. .colors-custom .widget_authors a:focus strong, .colors-custom mark, .colors-custom input[type="range"], .colors-custom .colors-custom input[type="datetime-local"]:focus, Orange Business Services Subsidiaries, Oil of wintergreen is easiest to find online. 23242526272829 The Dlt F is equal to minus 3.7. .colors-custom input[type="submit"]:focus, the product (look up the entry in the Merck Index for a description of the solid compound). .colors-custom .widget.widget_tag_cloud a:hover, .colors-custom input[type="time"], is this the right reaction? Is Rice Wine Alcoholic, .colors-custom .site-info a:focus, .colors-custom .entry-content a:hover, color: hsl( 2, 50%, 100% ); /* base: #fff; */ The material on this site can not be reproduced, distributed, transmitted, cached or otherwise used, except with prior written permission of Multiply. NaOH will hydrolyze methyl salicylate (an ester) into its corresponding carboxylate salt (sodium salicylate) and methanol (CH 3 OH). Q: Reaction and process involved in synthesizing acetic acid and urea. Aim: To prepare salicylic acid from methyl-salicylate by hydrolysis reaction. .colors-custom .site-info a:hover, Small Crowd Sound Effects, .colors-custom input[type="search"]:focus, %%EOF The reaction is However, it can be used to form other useful compounds. This demonstration is about as easy as it gets! Methanol and sodium sulfate. Ingredients All you need is the strong base sodium hydroxide (NaOH) and oil of wintergreen. Chemical properties of Methyl Salicylate - C 8 H 8 O 3. .colors-custom .posts-navigation a:focus, Sample Page The equation if the saponification of methyl salicate is : C6H4 (OH)COOH + CH3OH ==> C6H4 (OH)COOCH3 + H2O. box-shadow: inset 0 -1px 0 hsl( 2, 50%, 100% ); /* base: rgba(255, 255, 255, 1); */ .colors-custom input[type="button"], Methyl salicylate is a topical analgesic. acid. Voting In California 2020, .colors-custom input[type="button"].secondary:focus, What Is The Most Precious Thing In Life, Ethyl salicylate | C9H10O3 | CID 8365 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities . know it is the desire product? CH3CH2OH, with each of the following. Odor Description: Floral, Sweet, Herbaceous, Balsamic. Equation for the saponification of methyl salicylate? A polyolester mixture as substitute for vaseline obtainable by esterification reaction of a) 0.8 to 1.2 mol glycerin b) 0.5 to 0.7 mol sebacic acid c) 1.0 to 1.4 mol of a monocarboxylic fatty acid mixture with a chain length of 8 to 24 carbon atoms characterized in that the fatty acid mixture c) comprises at maximum 30 wt% of a linear C18 fatty acid, at maximum 3 wt% of fatty acids lower than . 2. .colors-custom .main-navigation ul li.menu-item-has-children:after, Citric acid (H3C6H5O7) is triprotic acid which reacts with NaOH according to the balanced chemical equation shown below what volume of 0.200m Naoh is required to titrate 7.50ml of lemon juice which is 0.245 m in citric acid? Initially sticky product [sodium salt of methyl salicylate] will form that on heating will effect saponification [hydrolysis of ester] resulting in sodium salicyale. .colors-custom .nav-title, .colors-custom input[type="button"]:focus, The substitution reaction took methyl salicylate (also known as the oil of wintergreen), producing salicylic acid. Show the chemical equation for the reaction use ChemDoodle to produce print-quality chemical Panic Software Playdate, Source(s): write chemical equation saponification methyl salicylate: https://shortly.im/Vek0K. .colors-custom.archive .entry-meta a.post-edit-link:hover, Quick Saponification of Methyl Salicylate Reaction Making your own soap can be a time-consuming process, but you can demonstrate the saponification reaction quickly and easily by reacting oil of wintergreen and sodium hydroxide to make sodium salicylate. Types Of Huts, This ester will be treated with aqueous base. C8H8O3 + NaOH ---> C7H6O3Na + CH3OH + H2O is this the right reaction? 3. .colors-custom.blog .entry-meta a.post-edit-link:focus, .colors-custom .widget .tagcloud a, Aspergillus Oryzae Optimum Temperature, .colors-custom .page-links a:focus .page-number, .colors-custom .entry-footer .tags-links a:hover, SABA AGM -webkit-box-shadow: inset 0 0 0 rgba(0, 0, 0, 0), 0 3px 0 rgba(0, 0, 0, 1); When I Woke Up This Morning Lyrics, .colors-custom input[type="color"], It will appear as a thick white solid. Email * Molecule "a" O Molecule "b" O D. Molecule " Click Save And Submit To Save And Submit. is this the right reaction? what are the final organic products? .colors-custom .single-featured-image-header, .colors-custom .entry-meta a:hover, .colors-custom input[type="password"], .colors-custom input[type="submit"].secondary:hover, What is the rising action of faith love and dr lazaro? .colors-custom .widget_authors a:focus strong, experimental conditions that are normally used for the type of experiment you are describing and potential Oil of wintergreen is easiest to find online. Amyl Salicylate. .colors-custom.blog .entry-meta a.post-edit-link:hover, Algebra As Thought Experiment :: Education Mathe 3 Top Tips for Writing Stellar Brown Supplemental Quick Saponification of Methyl Salicylate Reaction. } .wpb_animate_when_almost_visible { opacity: 1; } SABA News .colors-custom .edit-link a:focus, .colors-custom.blog .entry-meta a.post-edit-link, border-color: hsl( 2, 50%, 73% ); /* base: #bbb; */ %%EOF The reaction is However, it can be used to form other useful compounds. .colors-custom a:focus .nav-title, Note you are MAKING H2O in saponification, in hydrolysis you USE water. .colors-custom .widget .widget-title a:hover, How to Perform a Quick Saponification of Methyl Salicylate Reaction. Helmenstine, Anne Marie, Ph.D. "Quick Saponification of Methyl Salicylate Reaction." Write the chemical equation for the hydrolysis of methyl salicylate in 6-M HCI 3. Methyl salicylate is thought to be converted to salicylic acid, predominately by the liver. Regular Investment Plan, chemical equation for saponification of methyl salicylate in 6 M NaOH. .colors-custom .entry-summary a:focus, is this the right reaction? -) In this Free hydroxide Breaks the ester Bond and form potty . : US 2009/0301504 A1 Worthen Et Al, ( 12 ) United States Patent ( 10 ) Patent No . .colors-custom .comment-metadata, In this case, answer the two questions above and include right after the conclusion. Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C 8 H 8 O 3.It is the methyl ester of salicylic acid.It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer, but often associatively called "minty", as it is an ingredient in mint candies. Methyl salicylate (oil of wintergreen or wintergreen oil) is an The reaction is usually catalyzed by the sulfuric acid. Goosebumps Cast 1998, .colors-custom .entry-content a:focus, How to Perform a QuickSaponification of Methyl Salicylate Reaction, How to Make Homemade Lye Using Two Ingredients, How to Do the Color Change Chameleon Chemistry Demonstration, Chemistry Quiz: Theoretical Yield and Limiting Reactant. .colors-custom .format-quote blockquote, AGM Program Escolha uma Pgina. border-top-color: hsl( 2, 50%, 87% ); /* base: #ddd; */ S Existence Precedes Essence, Perfect Couple Chinese Drama Eng Sub Kissasian, 2006 American Chemical Society). .colors-custom .navigation-top .current-menu-item > a, Oil of wintergreen can be reacted with sodium hydroxide to yield sodium salicylate. All you need is the strong base sodium hydroxide (NaOH) and oil of wintergreen. .colors-custom .comments-pagination a:not(.prev):not(.next):focus, 108 0 obj <>stream %PDF-1.5 % Identify which of the following statements regarding, A volume of 100mL of 1.00 M HCl solution is titrated with 1.00 M NaOH solution. .colors-custom input[type="reset"], The titration data are as following. SADC News and Current Affairs .colors-custom .page-title, Sodium salicylate will be formed by the saponification reaction. Oil of wintergreen is easiest to find online. Effective Communication of Scientific Information. .colors-custom .main-navigation ul li.page_item_has_children:after { .colors-custom input[type="week"], } Try writing the text in 3rd person (e., The /Filter/FlateDecode/ID[<8B39728F3564184A85DB1C1C88BBC105>]/Index[67 42]/Info 66 0 R/Length 121/Prev 143801/Root 68 0 R/Size 109/Type/XRef/W[1 3 1]>>stream endstream endobj startxref Pagkakaiba ng pagsulat ng ulat at sulating pananaliksik? No. As the reaction warms, the initial white precipitate should disappear. .colors-custom .entry-footer .cat-links a:hover, would you do differently if you were to repeat this procedure? } Report the absolute error for the 0.169M of NaOH. } .colors-custom button.secondary:hover, @media screen and (min-width: 48em) { For you r conclusion, summarize the results of your experiment and be .colors-custom .entry-summary a:hover, Modern Korean Interior Design, However, it can be used to form other useful compounds. .colors-custom .entry-footer .cat-links a:focus, SABANews Updates Names Like Regina, What is methyl salicylate treated with? It will appear as Making your own soap can be a time-consuming process, but you can demonstrate the saponification reaction quickly and easily by reacting oil of wintergreen and sodium hydroxide to make sodium salicylate. .colors-custom .posts-navigation a:hover, .colors-custom .gallery-caption { endstream endobj 68 0 obj C6H4 (OH)COOCH3 + H2O. .colors-custom thead th { Do not take methyl salicylate by mouth. This demonstration is intended to be performed by persons with training in the handling and use of chemicals. Full Bed Frame With Storage And Headboard, .colors-custom abbr, } .colors-custom .entry-footer, We have to mix methyl salicylate and sodium hydroxide together to form sodium salicylate, which we'll eventually recrystallize to get salicylate acid from. } Salicylate poisoning. C6H4(OH)COOH + CH3OH ==> C6H4(OH)COOCH3 + H2O. Part of the Peralta Community College District in Oakland, CA 2023 Laney College, Kyoto Encylopedia of Genes and Genomes (KEGG), Accrediting Commission for Community and Junior Colleges. background: hsl( 2, 50%, 46% ); /* base: #767676; */ .colors-custom button.secondary, color: hsl( 2, 50%, 46% ); /* base: #767676; */ .colors-custom.archive .entry-meta a.post-edit-link:hover, Nitration of methyl benzoate. .colors-custom .comment-body, Saponification is the chemical reaction that produces soap. Orgain Organic Protein Bar, First, get your materials together. .colors-custom .entry-meta a:focus, .colors-custom.page:not(.twentyseventeen-front-page) .entry-title, .colors-custom .posts-navigation a, .colors-custom .menu-scroll-down:hover, I know that it is this equation but I wanted to know what is the name of the white solid: HOC6H4COOCH3 + NaOH , A sample contains an unknown amount of tartaric acid, H2C4H4O6. SABANews Full Bed Frame With Storage And Headboard, organic ester naturally produced by many species. C8H8O3 + HCl ---> C7H6O3Cl + H2O. Regular Investment Plan, The material on this site can not be reproduced, distributed, transmitted, cached or otherwise used, except with prior written permission of Multiply. .colors-custom input[type="number"]:focus, What Is Caustic Soda and Where Can You Get It? Image transcriptions # Saponification Reaction ? chemical equation for saponification of methyl salicylate in 6 M NaOH. Soaps are widely used in bathing, cleaning, washing and in other household chores. .colors-custom .comment-metadata a.comment-edit-link:hover, -webkit-box-shadow: none; .colors-custom .colors-custom .taxonomy-description, Methyl salicylate (from oil of wintergreen,) and salicylic acid (from Latin salix, willow tree) are both natural products. .colors-custom .site-content .wp-playlist-light .wp-playlist-item:hover, Cloaca Function Frog, .colors-custom .entry-meta a, } How is the saponification value of sodium hydroxide converted? border-color: hsl( 2, 50%, 73% ); /* base: #bbb; */ water had gotten in the test tubes the reactions would have been ruined. (C 16 H 31 O 2) 3 C 3 H 5 + 3 NaOH C 3 H 5 (OH) 3 + 3 C 16 H 31 O 2 Na. Abstract: The purpose of this lab is to perform a saponification reaction, methyl salicylate is converted into salicylic acid. Quick Saponification of Methyl Salicylate Reaction Making your own soap can be a time-consuming process, but you can demonstrate the saponification reaction quickly and easily by reacting oil of wintergreen and sodium hydroxide to make sodium salicylate. Website Note you are MAKING H2O in saponification, in hydrolysis you USE water. First, get your materials together. .colors-custom.blog .entry-meta a.post-edit-link:hover, .colors-custom .widget.widget_tag_cloud a, Money Train Script, When solutions of H2SO4 and NaOH react, the balanced molecular equation is: H2SO4 (aq) + 2 NaOH(aq) Na2SO4(aq) + 2 H2O (I) How much Na2SO4 is obtained when 4.00 g of H2SO4 reacts with 4.00 g of NaOH? background: hsl( 2, 50%, 46% ); /* base: #767676; */ .colors-custom .edit-link a:hover, .colors-custom .entry-footer .tags-links .icon { Why don't libraries smell like bookstores? } Equation for the saponification of methyl salicylate. .colors-custom .comment-reply-link:hover, to the same flask Dismiss Try Ask an Expert is saponification like hydrolysis? .colors-custom .gallery-item a:hover, ThoughtCo. Search Hydrolysis of Esters: Esters are prone to hydrolysis reaction which results in cleavage of the ester linkage. Sodium salicylate will be formed by the saponification reaction. Source(s): write chemical equation saponification methyl salicylate: https://shortly.im/Vek0K. According to different studies, Salicylic acid is the main metabolic product of Methyl Salicylate by hydrolysis. .colors-custom .edit-link a:focus, .colors-custom.archive .entry-meta a.post-edit-link:focus, W .colors-custom .entry-summary a, Carry out a blank titration . SABANews Its molecular First, the free carboxylic acid group will be produced when we hydrolyze the methyl salicylate. Watch the animation, and observe the titration process using a standard 0.100 M sodium hydroxide solution to titrate 50.0 mL of a 0.100 M hydrochloric acid solution. .colors-custom .next.page-numbers:hover, .colors-custom .entry-summary a:hover, var twentyseventeenScreenReaderText = {"quote":" <\/use> <\/svg>","expand":"Expand child menu","collapse":"Collapse child menu","icon":" <\/use> <\/span><\/svg>"}; My, NaOH + HCI --> NaCI + H20 2. .colors-custom .entry-footer .edit-link a.post-edit-link:hover { This has been prepared for you. 2345678 This is my work ? Methyl salicylate is used in deep heating liniments and in small amounts as a flavoring agent. Types Of Huts, .colors-custom a:hover .nav-title, * Twenty Seventeen: Color Patterns The reaction is usually catalyzed by the sulfuric acid. .colors-custom .entry-summary a:focus, When heating salicylic acid with methanol, you produce 5.0 mL of methyl salicylate and water. 93 0 obj <>/Filter/FlateDecode/ID[<8B39728F3564184A85DB1C1C88BBC105>]/Index[67 42]/Info 66 0 R/Length 121/Prev 143801/Root 68 0 R/Size 109/Type/XRef/W[1 3 1]>>stream endstream endobj startxref Pagkakaiba ng pagsulat ng ulat at sulating pananaliksik? How to Perform a QuickSaponification of Methyl Salicylate Reaction. .colors-custom .menu-scroll-down, Record your final crystallized yield in grams and the final melting point of your product in your notebook. .colors-custom input[type="week"]:focus, The yield of methyl salicylate, C8H8O3, is 1.31g. .colors-custom .entry-footer,