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Oil of Wintergreen Synthesis ..
Oil of Wintergreen (methyl salicylate)– aromatic ester, synthesized by Fischer Esterification.
Common learning lab, used to associate product with scent, gives experiment “immediate relevance” (Hartel & Hanna).
Most widely used technique for creating esters (Hartel & Hanna).
General reaction: Green Techniques...
“Preparation of Oil of Wintergreen from
Commercial Aspirin Tablets – A Microscale Experiment Highlighting Acyl Substitutions.” Journal of Chemical Education.
Preparation of Methyl Benzoate | Topiea Reagen - …
our actual results TMS TMS NMR solvent(Chloroform) NMR solvent(Chloroform) NMR solvent(Chloroform) Water Water Percent yield and IR spectroscopy could not be obtained because there wasn't enough final product from either experiment
NMR spectroscopy was inconclusive for both experiments because our final product was too diluted in the NMR solvent
C-NMR showed only the NMR solvent
H-NMR showed NMR solvent, water, and TMS Small peaks observed for our final product in the expected regions but because of how diluted it was they are hard to see Both boiled off; NMR analysis run from remaining product on boiling chips Oil of Wintergreen: Synthesis and NMR Analysis.
ft., former Hercules/PFW facility in Middletown, NY; Fleurchem produces a full range of natural isolates, synthetic chemicals & specialities, essential oils and flavors.
Detailed mechanism for the preparation of methyl salicylate?
2 reactions carried out:
H2SO4 – catalyzed
H3PO4 – catalyzed (less strong, less potentially harmful)
Micro-scale reaction – less waste
Extraction with diethyl ether (instead of methylene chloride) – less toxic Reflux-condensation setup: synthesis of wintergreen oil Salicylic acid, methanol, sulfuric/phosphoric acid
Stirred in hot water bath, while cooling steam with water current, for 60 minutes
Removed from heat, cooled to ambient temperature Liquid-Liquid extraction: Diethyl ether and DI water added to reaction mixture, organic layer (bottom) extracted
Organic layer washed 3x with sodium bicarbonate (vented to release CO2 gas), extracted after last wash, and solvent (ether) boiled off
NMR spectra analyses performed on remaining product (1) (2) Hartel, A.M.; Hanna, J.M.
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