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CHEM 237 Exp 6 Formal Lab Report- ISHAN JOSHI.docx - CHEM...

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CHEM 237 Experiment 6Multi-Step Synthesis of FragrancesIshan Joshi, Section ABATA: Thomas Trzupek, Hannah Way
IntroductionThe objective of the lab was to carry out the multi-step synthesis of a benzyl ether derivative.Many commercially available fragrances contain benzyl ethers, including but not limited tomethyl diantilis, which can be synthesized from ethyl vanillin and methanol. Ethyl vanillin isa derivative of vanillin, which in turn is the primary component of vanilla extract. Methyldiantilis was not the benzyl ether derivative synthesized in lab, but it serves as a goodexample of the kinds of compounds perfume makers experiment with in order to producevarious kinds of scents to stimulate the olfactory nerves. The branch of chemistry devoted tothe synthesis and study of compounds such as methyl diantilis is called organolepticchemistry.The benzyl ether derivative in this lab was synthesized by first using sodium borohydride toreduce a benzaldehyde derivative to make a benzyl alcohol derivative and acidifying withhydrochloric acid. Then, an etherification reaction with ethanol was carried out to make thebenzyl ether derivative. A reflux condenser was set up to push the reaction forward, and TLCor thin-layer chromatography was utilized to track the reaction’s progress and whether or notthe product had been formed. TLC was also used to select the ideal eluent for columnchromatography, which was used to purify the product.Column chromatography is a method to isolate a compound from a mixture of compounds byfirst dissolving that mixture in a mobile phase, or eluent, and then pouring that dissolvedmixture into a cylindrical glass tube containing a stationary phase. In this case, the stationaryphase was silica gel and the mobile phase was a mixture of liquid hexane and ethyl acetate.The impurities dissolved in the eluent were adsorbed by the silica gel, and the benzyl etherderivative was eluted through into a test tube. TLC was used to monitor the collectedfractions of eluent to test which one of them contained the benzyl ether derivative. Thefraction in question was then subjected to rotary evaporation to isolate the pure benzyl etherderivative.Column chromatography is an immensely useful and popular technique to purify isolatedcompounds. Many kinds of substances are used as mobile and stationary phases to isolatecertain compounds. For example, to isolate the amino acids D-glutamic acid and D-alaninefrom protein samples, a new method of column chromatography called liquidchromatographic assay was developed that utilizes beta-cyclodextrin as the mobile phase(Rizzi et al, 1992). It has a higher reliability of results when it comes to tracking minutesamples of the amino acids of interest in the biological samples assayed.

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Term
Fall
Professor
Denofrio
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