The synthesis of aspirin and wintergreen oil were both driven by an acid- catalyzed esterification reaction aspirin was synthesized from salicylic acid and acetic anhydride while wintergreen oil was synthesized from salicylic acid and methanol6,7 both reactions were catalyzed with concentrated sulfuric acid the ir spectra. Table of contents aspirin synthesis significance of determining aspirin purity synthesis of salicylic acid from wintergreen oil procedure risk assessment synthesis of aspirin from salicylic acid procedure risk assessment. View lab report - synthesis of salicylic acid from wintergreen oil from che 311 at american international synthesis of salicylic acid from wintergreen oil organic chemistry 311 abstract amoya. Preparation of oil of wintergreen from commercial aspirin tablets procedure medicinal and to prepare it from acetyl salicylic acid (which is the main constituent of aspirin tablets) you must first cleave the acetate ester at the phenolic oh this can be also done in synthesis of methyl salicylate from a spirinpdf 39710 kb.
Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula c6h4(oh)(co2ch3) it is the methyl ester of salicylic acid it is a colorless, viscous liquid with a sweet odor it is produced by many species of plants, particularly wintergreens it is also synthetically produced, used as a fragrance. The methyl ester also occurs widely in nature it is the chief constituent of oil of wintergreen salicylic acid was first prepared by the italian chemist raffaele piria in 1838 from salicylaldehyde in 1860 the german chemists hermann kolbe and eduard lautemann discovered a synthesis based on phenol and carbon dioxide. Rationale the two-step conversion of oil of wintergreen (methyl 2- hydroxybenzoate) into salicylic acid (5) and then into aspirin (6) serves as an introductory example of multistep sequen- tial synthesis it also provides practice in molecular pattern synthesis of aspirin a general chemistry experiment john olmsted iii.
However, in the late 1900's in germany, the bayer co began chemical production of the acetyl ester of salicylic acid, which they trademarked as aspirin ” the generic form of this drug is commonly called acetylsalicylic acid (asa) another ester of salicylic acid, the methyl salicylate, commonly known as oil of wintergreen. Methyl salicylate (oil of wintergreen this is the amount of ms that you use to calculate the amount of base to use for the hydrolysis and to calculate the theoretical yield of salicylic acid you will need a slight excess so that the solution is definitely acidic in order to precipitate the product, salicylic acid.
Salicylic acid can be methylated using eg methanol to yield methyl salicylate synthetic methyl salicylate, just as its natural counterpart, shows as a colorless liquid with a characteristic scent of wintergreen it is very cheap as a bulk ingredient that is produced in huge amounts in china, usually sold at a. Synthesis of salicylic acid from wintergreen oil by: matthew rook introduction: experiment 3: synthesis of salicylic acid from wintergreen oil purpose: 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.
Methyl salicylate is an ester salicylic acid derivative found in many plants 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 it can be used as an additive in food, because it has a flavor similar to mint. Salicylic acid by itself has medicinal values but is extremely corrosive to the upper intestinal tract and stomach continued use of pure salicylic acid leads to ulcers of the intestine the chief component you will be using is methyl salicylate, which is the chief ester in the flavour oil of wintergreen it is used to a considerable. The purpose of this experiment was to perform a base-catalyzed hydrolysis reaction while converting oil of wintergreen to salicylic acid the full balanced molecular equation for the salicylic acid synthesis is c8h8o3 + 2 naoh + h2so 4 - c4h6o3 + na2so4 + ch3oh + h2o an illustrated equation.
(systemic acquired resistance/salicylic acid glucoside/benzoic acid 2- hydroxylase/udp-glucose:salicylic acid glucosyltransferase) hyung-il lee, jose leon result of a de novo protein synthesis in tmv-inoculated tobacco ester, is found in oil of wintergreen (51), in the leaves of oats (52), red clover ( 53), fig (54),. On methyl salicylate and salicylic acid see experiment 43 in pavia, (pp 372-375) see the mechanism and discussion in klein on saponification of esters, sections 2111 (2nd edition) general methyl salicylate (from oil of wintergreen,) and salicylic acid (from latin salix, willow tree) are both natural products methyl salicylate. This page contains syntheses of salicylic acid because these are original works, it is asked that the texts not be edited from their original form except for clarity's sake suggestions or improvements can be put in the notes section below their respective synthesis this section details.