Synthesis of Acetophenetidin by Amide Synthesis

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The goals of this experiment are to determine if the products derived from amide synthesis and Williamson Ether Synthesis are identical, and if one of the synthetic routes is more advantageous than the other. In Part 1, an attempt to synthesize acteophenetidin crystals by amide synthesis was made. We began by removing the colored impurities from the p-Phenetidine (reddish-brown) by placing 2g of the sample in 38 mL of hydrochloric acid and heating the solution to boiling point. Upon reaching just below boiling point, decolorizing carbon was added to the solution, and the solution was allowed cooled for 2-3 minutes. The dark black solution was filtered through a gravity filtration system, leaving dark residue behind on the filter paper, and colorless to slightly pink liquid in the beaker. Then, 9 mL of sodium acetate buffer, to maintain a relatively constant pH and 1.8 mL of acetic anhydride were added to the solution, and then it was mixed and heated for about 5 minutes. Then, to induce crystallization, the beaker was placed in an ice bath. The slightly white, powdery crystals were collected using the Buchner funnel, and allowed to dry in the funnel and then on a watch glass. The mass of the crude sample collected was 2.84 g, providing the percent yield (Show calculation) to be 142%. I believe that the mass of the crude sample was inaccurate due to liquid remaining in the sample of crystals after drying. To prevent that next time, I’ll be sure to let the sample of crystals dry for a longer of period of time. The measured melting point of the crude sample was 130C – 133.4C, slightly below what is expected of pure acetophenetidin (133C – 136C).