Synthesis of salicylic acid from wintergreen oil

Your synthetic target is to prepare 2.

Synthesis of salicylic acid from wintergreen oil

Together we'll explore those organic chemistry labs we love oh so very much. In the event you find this near sunrise filled with anxiety, rage and confusion I hope this gives you a hand.

The purpose of this experiment was to perform a base-catalyzed hydrolysis reaction while converting oil of wintergreen to salicylic acid. An illustrated equation showing compounds to be isolated or synthesized is shown below.

Salicylate Toxicity from Ingestion and Continued Dermal Absorption

Methyl salicylate has a relatively weak phenol and carboxylic functional groups that are important in this experiment; it also has a mint like smell smell, and reacts rapidly with NaOH.

Structures of molecules mentioned above are shown below. Procedure All procedures were carried out under a hood, all individuals involved wore nitrile gloves and safety goggles. Glassware was cleaned, rinsed with deionzed water and if necessary acetone before usage.

The pellet form of the NaOH made it difficult to acquire the. After the pellets dissolved. A boiling stone was then dropped to the bottom of the round bottom flask.

Next, using grease on the glass joint, a water jacketed condenser was added to the round bottom flask. They were connected and held in place by a screw cap at the joint of intersection between the two.

Two water tubes were attached to the condenser, the top arm attached to a tube allowing for water to go out, the bottom arm of the condenser was connected to a tube lead from the water source in the hood, allowing for the water to come in and run through.

Synthesis of salicylic acid from wintergreen oil

A clamp was used to hold the apparatus steady and hold fast to a vertical rod in the hood. The mixture was heated for about 15 minutes as the white solid dissolved. After reflux, the equipment was allowed to cool to room temperature by separating it from the heat source, it sat till it was only slightly warm and comfortable to handle.

The condenser was removed. The contents of the round bottom flask then underwent vacuum filtration through a Hirsch Funnel fit with filter paper and connected with an integral adapter to a 25mL filter flask.

CDC - SALICYLIC ACID, METHYL ESTER - International Chemical Safety Cards - NIOSH

The crude product from the Hirsch funnel was then transferred to weigh paper using a spatula. The salicylic acid crystals were then placed in a 10mL Erlenmeyer flask. Next, 5mL of water were added to the Erlenmeyer flask containing the crystals.

The solution was put on the hot plate till the solid dissolved and was immediately taken off. The flask and its contents were allowed to sit at room temperature while crystallization occurred.


The crystals were collected via a second filtration using a Hirsch funnel with the same set up as the one done earlier in the experiment. Upon completion of the filtration the crystals were placed in an empty vial and stored for a week.

The following week the crystals were packed into a capillary tube with only one open side. The sample was placed in apparatus, Mel Temp, that provided a magnified view of the sample and temperature, allowing for the assessment of the samples melting point and range. Another sample was prepared with acetone with deutero Hydrogen by an instructor.

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Samples from multiple lab groups ran through the machine, the goal was to learn how the C NMR helps determine molecular structure, and look at the induced magnetic field. Things that are good to know for this lab: Finding the limiting reagent plug and chug Note: There is a 1: Note, Methyl salicylate is the limiting reagent; this will be used to calculate the theoretical yield.

Referring to the balanced molecular equation there is a 1: After NMR give two pieces of evidence that salicylic acid was the solid produced by reacting methyl salicylate with the aqueous base.

Which piece of evidence gives the direct structural information? Which gives only indirect evidence? C13 NMR of methyl salicylate has 8 unique carbon peaks, while salicylic acid has 7. The C that is lost was bonded to 2 Oxygen molecules making it down stream whihc is congruent with the chemical equaiton.

C13 NMR gives indirect structural information.Jan 24,  · Synthesis of Methyl Salicylate (Oil of wintergreen) THEORY Methyl salicylate can be produced through esterification of salicylic acid with methanol in the presence of acid catalyst, particularly sulfuric acid, providing a large amount of hydrogen ions and speeding up the rate of reaction.

Methyl salicylate, which is commonly referred to as oil of wintergreen and smells minty, is a compound having an ester function. It was first isolated in by extraction from a plant (Gaultheria spp.) which is in the mint family. In this experiment you will synthesize salicylic acid from methyl salicylate.

Methyl salicylate is also a botanical extract. It is the major constituent of oil of wintergreen, which makes up over 90% of the essential oil from the wintergreen plant. Abstract. Methyl salicylate, or wintergreen oil, is an organic ester naturally produced by the wintergreen plant group, and commonly made by the esterfication of salicylic acid with methanol.

salicylic acid sulfuric acid 3. For the synthesis of each ester, add 20 drops of the alcohol and 10 drops of the carboxylic acid (or enough solid on the end of a spatula that is about the size of a large The odors for the esters in this lab include: banana oil, oil of wintergreen, artificial peach flavor, pineapple oil, orange oil, and an.

Methyl salicylate is an organic ester easily recognized by its odor and is known as oil of wintergreen and involves a reaction of the -COOH group of salicylic acid. It can be used commercially as an antipyretic, an analgesic, or as a non-steroidal anti-inflammatory drug (NSAID).

Overcoming Organic Chemistry: Synthesis of Salicylic Acid