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Synthesis of Methyl Salicylate | Ester | Alcohol

This process is widely used in industrial and laboratory distillations.Mass of methyl salicylate collected was 14 g.

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Synthesis of Aspirin and Oil of Wintergreen - …

The quantity in the denominator (2.5 g) represents the theoretical yield of aspirin based on the moles of salicylic acid and acetic anhydride used in the synthesis.

Coquoz JL, Buchala A, Metraux JP 1998 The biosynthesis of salicylic acid in potato plants.

Rao MV, Paliyath G, Ormrod DP, Murr DP, Watkins CB 1997 Influence of salicylic acid on HO production, oxidative stress, and HO-metabolizing enzymes: salicylic acid mediated oxidative damage requires HO.

Synthesis of Aspirin and Oil of Wintergreen ..

Penninckx IAMA, Eggermont K, Terras FRG, Thomma BPHJ, De Samblanx GW, Buchala A, Metraux J-P, Manners JM, Broekaert WF 1996 Pathogen-induced systemic activation of a plant defensin gene in follows a salicylic acid-independent pathway.

Compare your laboratory aspirin with several brands of commercial aspirin.[The laboratory synthesized aspirin should have an absorbance >0.5 at 540 nm.

of Part 1 for this experiment was used for the synthesis of Aspirin

Determine weight of methyl salicylate obtained and calculate percent yield.
Data and Results
Weight of methyl salicylate - 13.65 g

Theoretical Yield - 30.38 g

Percent Yield - 44.93%
Conclusion
Methyl salicylate is an organic ester naturally produced by many species of plants, specifically wintergreens.


Precursor: Salicylic Acid
Aspirin takes away pain by inhibiting or preventing the growth of inflammation causing cells
History
Circa 1800: Salicylic Acid- discovered from bark of Willow tree
1853: primitive form of Aspirin
1897: synthesized by Felix Hoffman under Bayer
1899: Bayer mass produces
How to manufacture Aspirin:
-weighing of ingredients (Corn starch, water & lubricant -> binding agent and fillers, acetylsalicylic acid )
-mixing - mixes ingredients, takes out air w/ glen mixer -> "Slugs"
-drying-forcing mixture by hand on mesh or use of fitzpatrick mill
-compression
-testing and packaging
*lubricants-hydrogenated vegetable oil, stearic acid, talc, or aluminum stearate
Aspirin
Acetylsalicylic Acid
QUALITATIVE TESTS
Medicine
Relieves pain
Different reactions
Aspirin industry
Social Issue
When you use,
DON'T ABUSE!
similar drugs:
Ibuprofen - same potency but does not upset stomach as much
Naproxen - same potency, stays in the body 6 times longer.

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  • Synthesis of Aspirin: Lab Analysis - Odinity

    Molders W, Buchala A, Metraux J-P 1996 Transport of salicylic acid in tobacco necrosis virus-infected cucumber plants.

  • A Student Researched Lab Experiment about the synthesis of Aspirin

    Synthesis of Methyl Salicylate - Download as Word Doc (.doc / .docx), PDF File (.pdf), Text File (.txt) or read online.

  • Synthesis of Methyl Salicylate from Aspirin - Yumpu

    Synthesis description for preparation of methyl salicylate (wintergreen oil)

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The Synthesis of Aspirin by Pianne Sinfuego on Prezi


This will allow crystallization upon cooling.
CONVERSION OF SALICYLIC ACID INTO ASPIRIN
Salicylic Acid + Acetic Anhydride
+ Sulfuric Acid = Aspirin
ACETYLSALICYLIC ACID
METHYL SALICYLATE
SODIUM HYDROXIDE
Caustic Soda
Lye
Different industries: Cleaning, food, paper
ETHYL ACETATE
SULFURIC ACID
Often used as a cleaning agent
Highly corrosive
Strong odor
Used in the experiment as a mineral acid
PREPARATION OF SALICYLIC ACID
HYDROXAMIC ACID TEST
Useful for detecting esters
Red-violet (+)
Detects the presence of Acetylsalicylic acid
FERRIC CHLORIDE TEST
Abridged version of Hydroxamic acid test
Phenols: Purple, red, green
Enols: Red, tan, violet
Yellow (-)
Aspirin comes from Salicylic Acid, which comes from the bark of Willow trees.

THE SYNTHESIS OF ASPIRIN (Acetylsalicylic Acid) INTRODUCTION ..

They are derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol.
Experiment 7: Synthesis of Ester Methyl Salicylate
Esters, whether artificial or natural, are wide used flavorings and perfumes.
used, in high concentrations, as a rubefacient and analgesic in deep heating liniments (such as Bengay) to treat joint and muscular pain
used, in low concentrations (0.04% and under), as a flavoring agent in chewing gum and mints
used as a simulant or surrogate for the research of chemical warfare agent sulfur mustard, due to its similar chemical and physical properties
used as an antiseptic in Listerine mouthwash produced by the Johnson & Johnson company.
Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children.
To become familiar with the method and principle involved in reflux
Materials
Boiling chips
Pipette
Rubber aspirator
Graduated cylinder
Spatula
Stirring rod
Evaporating dish
250-mL beaker
500-ml beaker
Iron ring
Round bottom flask
Condenser
2 rubber tubings
Separatory funnel
Vials
Bunsen burner
Tripod
Water bath
Clamps
Iron stand
Synthesis
Procedure
Place 60 mL methanol, few boiling chips, and 27.6 g salicylic acid in a round bottom flask.

synthesis of aspirin from methyl salicylate

A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate, which is equivalent to more than twenty-three 300 mg aspirin tablets.
used for providing fragrance to various products and as an odor-masking agent for some organophosphate pesticides
naturally found in the bark of sweet birch tree (
Betula lenta
)
Esters are chemical compounds consisting of a carbonyl adjacent to an ether linkage.

The synthesis of aspirin is a multi-billion dollar a year chemical.

MeSA is a constituent of the floral scent of flowers (Dudareva et al, 1998), and is synthesized by an -adenosylmethionine-dependent salicyclic acid carboxyl methyltransferase that adds a methyl group to the carboxyl group of salicylic acid, not the -OH group.

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