Beta Citronellyl Tosylate Essay

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Laboratory Experiment pubs.acs.org/jchemeduc A Two-Step Synthesis of the Laundry Detergent Perfume Additive β‑Citronellyl Tosylate Cheryl M. Mascarenhas* Department of Chemistry, Benedictine University, Lisle, Illinois 60532, United States S * Supporting Information ABSTRACT: A two-step synthesis of the compound β-citronellyl tosylate is described. The final product, synthesized by the reduction of β-citronellal with sodium borohydride followed by a solvent-free tosylation, is used as a perfume precursor and additive to laundry detergent. This project can be performed in two weeks in a typical second-year organic chemistry teaching laboratory. It exposes students to perfume chemistry, a topic not typically discussed in an organic chemistry course. Moreover, the solvent-free tosylation step of the reaction leads pedagogically to a discussion about green chemistry. KEYWORDS: Second-Year Undergraduate, Laboratory Instruction, Organic Chemistry, Hands-On Learning/Manipulatives, Alcohols, Aldehydes, Green Chemistry, NMR Spectroscopy, Thin Layer Chromatography, Synthesis Scheme 1. Synthesis of β-Citronellyl Tosylate I t has been a tradition in chemical education to use examples of compounds in “real-world” applications to illustrate esoteric concepts.1 Although many of the applications in textbooks and the chemical educational literature are biological and medicinal in nature, examples using soaps,2 essential oils, perfumes, and cosmetics can be traced back to the 1940s. There are several earlier articles published in this Journal that describe the chemical composition of essential oils,3 whereas more recent lab experiments focus on the synthesis of perfumes.4,5 Sulfonates of several compounds are used as additives in the perfume industry, especially for laundry and other cleaning detergents. One such sulfonate used as an additive to

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