Preparation of Oil of Wintergreen from Commercial Aspirin Tablets. A Microscale Experiment Highlighting Acyl Substitutions

Hartel, Aaron M.; Hanna, James M.

doi:10.1021/ed086p475

Cited by 10 publications

(7 citation statements)

References 14 publications

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“…Concentrated H 2 SO 4 was added to the aspirin solution, and it was either refluxed for 90 min or heated in a scientific microwave system at 120 °C for 5 min. The MS was obtained in yields approaching 70% [ 22 ].…”

Section: Resultsmentioning

confidence: 99%

Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation

et al. 2022

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SiO2–SO3H, with a surface area of 115 m2/g and pore volume of 0.38 cm3g−1, and 1.32 mmol H+/g was used as a 20% w/w catalyst for the preparation of methyl salicylate (wintergreen oil or MS) from acetylsalicylic acid (ASA). A 94% conversion was achieved in a microwave reactor over 40 min at 120 °C in MeOH. The resulting crude product was purified by flash chromatography. The catalyst could be reused three times.

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Section: Resultsmentioning

confidence: 99%

Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation

et al. 2022

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“…Direct insertion spectra were measured at 70 eV. Quantitative analyses were performed on a Shimadzu GC-2010 gas chromatograph equipped with a ame ionization detector [30]. 1 H-and 13 C-NMR spectra were recorded on Bruker Avance 400 Spectrometers as has been previously described [30].…”

Section: Instrumentationmentioning

confidence: 99%

Dimethyl sulfate as methylation agent in highly regioselective synthesis of methyl salicylate using sodium bicarbonate as a base in solvent-free medium

Freitas,

Nelson,

Sousa

et al. 2024

Preprint

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Methyl salicylate (MS), the principal constituent of Wintergreen oil (WO), was obtained from salicylic acid (SA) by regioselective methylation of the carboxyl group. A new procedure involved exclusive capture of carboxylic hydrogen (-COOH) through the use of the selective base, NaHCO3. and methylation via an SN2 mechanism employing the previously formed carboxylate as a nucleophile and the dimethyl sulfate [(CH3)2SO4 or DMS] as the electrophilic reagent or substrate in a solvent-free reaction process. The reagents were added separately. SA and NaHCO3 was added, followed by DMS after 30 min. The reaction involved the esterification by nucleophilic substitution in Csp3 with heating by a heating mantle. The reaction was accompanied by thin layer chromatography and gas chromatography. The conversion rate via GC was 100%, and the MS yield was 96%. The DMS used in excess was transformed into MeOH and H2SO4 during the washing with water. The MeOH was stored, and H2SO4 was transformed in Na2SO4 by neutralization with NaOH. Na2SO4 can be used as a desiccant. The simplicity of the procedure, readily available MS, short reaction times, excellent yield and mild reaction condition are other advantages of this protocol. Cytotoxicities of 50% and 64% for cultured S. aureus and metastatic melanoma cells, respectively, were observed for a concentration of 0.6 mg/mL of the MS produced, whereas no cytotoxicity against non-tumor cells was observed at this concentration, and this is considered to be the optimum concentration.

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“…Next, students are guided through a chemical synthesis where they transform the lead molecule aspirin into methyl salicylate, more commonly known as oil of wintergreen. Unlike previously published articles on the synthesis of oil of wintergreen from aspirin, , this experiment further investigates the starting material and product. On the basis of observations of physical properties before and after the synthesis, students see evidence that their reaction was successful and that their molecule has changed (solid to oil, bitter smell to minty smell, white color to colorless).…”

Section: Experimental Overviewmentioning

confidence: 99%

PharmaChemistry in the Classroom: A Drug-Discovery Experiment for the High School Chemistry or Biotechnology Classroom

Sega

Clarke²

2013

J. Chem. Educ.

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In this laboratory experiment, students were exposed to a real-world approach to science through learning about and simulating the processes by which drugs are designed and discovered. The students first synthesized oil of wintergreen from aspirin and analyzed the physical properties of both the starting material (aspirin) and product (oil of wintergreen) to validate that their reaction was successful. Second, unique to this lab experiment, students further scrutinized the synthesis by performing a biological assay investigating the antibacterial properties of their samples. Through the use of these analyses, students were able to play the roles of chemists, biologists, and team members involved in the drug-discovery pipeline. The results revealed to the students that small changes in molecular structure caused significant changes in medicinal activity. Through data analysis, discussion, and problem sets, students evaluated various steps of the experiment as they simulated the drug-discovery process.

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Preparation of Oil of Wintergreen from Commercial Aspirin Tablets. A Microscale Experiment Highlighting Acyl Substitutions

Cited by 10 publications

References 14 publications

Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation

Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation

Dimethyl sulfate as methylation agent in highly regioselective synthesis of methyl salicylate using sodium bicarbonate as a base in solvent-free medium

PharmaChemistry in the Classroom: A Drug-Discovery Experiment for the High School Chemistry or Biotechnology Classroom

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