THE REACTION
1. Dissolve trimyristin (0.5 g) in methanol (12 mL) in a 50 mL round bottom flask.
2. Add concentrated sulfuric acid (250 μL) to the flask, and heat the solution to reflux for 1 hour.
THE WORKUP
3. Cool the solution to room temperature and then pour it into 25 mL distilled water in a separatory funnel.
4. Extract the mixture with 25 mL ethyl acetate, and separate the two layers. Transfer the organic layer to a 50 mL Erlenmeyer flask.
5. Return the aqueous layer to the separatory funnel and extract it with a fresh 25 mL portion of ethyl acetate.
6. Remove the aqueous layer, and return the first organic layer to the funnel.
7. Wash the combined organic layers with brine (saturated NaCl). Remove the aqueous solution, and transfer the organic layer to a 125 mL Erlenmeyer flask.
8. Dry the organic layer over sodium sulfate.
9. Gravity filter the mixture into a preweighed 100 mL round bottom flask in order to remove the sodium sulfate. (Note: Pre-folded filter paper is available to you in the lab.)
10. Remove the solvent by rotary evaporation to give a clear oil. Determine the mass of the product.
PRODUCT ANALYSIS
11. Prepare a GC-MS sample by dissolving a single drop of your product into 2 mL ethyl acetate in a test tube. Your instructor/TA will assist you in obtaining the GC-MS data.
12. Obtain an IR spectrum of your product.
13. Save the remaining product in a test tube at your lab station.