A mixture of ground nutmeg (1.00 g) and tert-butyl methyl ether (3.0 mL) was added to a round-bottomed flask and gently boiled for ten minutes. After settling, the resulting liquid was cotton-filtered through a pipet, rinsed again with tert-butyl methyl ether (2.0 mL), and filtered as before into a tared 25 mL Erlenmeyer flask. The filtered solution was then evaporated gently to yield the crude product (0.763 g, 1.05 mmol, 76.3% recovery), which was subsequently recrystallized in acetone (15.26 mL) to yield a once-recrystallized product (0.147 g, 0.203 mmol, 19.3% recovery), isolated via vacuum filtration. Hydrolysis was performed in a clean round-bottomed flask through reflux of a solution of the trimyristin (0.060 g, 0.083 mmol), 6 M sodium hydroxide (2.0 mL), and ethanol (95%, 2.0 mL) gently for 45 minutes. The resulting contents of the flask were then poured into a 50 mL beaker containing 8 mL of water and concentrated hydrochloric acid (2.0 mL) was added dropwise while stirring. The beaker was then cooled in ice water for ten minutes while stirring, and vacuum filtration was used to collect the resulting myristic acid product (0.046 g, 0.201 mmol, 82.14% yield). During the hydrolysis portion of the experiment, the remaining trimyristin (0.086 g, 0.12 mmol) was recrystallized a second time to obtain a twice-recrystallized product (0.067 g, 0.093 mmol, 77.9% recovery), which was subsequently vacuum filtrated. The melting points of the once-recrystallized product (55 - 57 ℃), product of hydrolysis (54 - 55 ℃), and twice-recrystallized product (54 - 56 ℃) were then taken.
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