Honors Cup Synthetic Proposal Section: 251 Group Members: Brian Kang, Grace Lee, Daina Zeng, Kit Yuen Title: Synthesis of 1,1-dimethoxy Introduction: (what makes your target interesting?) In the food industry, our compound is a necessary part of creating nut aromas, specifically the hazelnut aroma. Investigation of the synthesis is potentially critical to minimizing the cost of production and enhancing food products such as coffee, wine, and chocolate. Manipulation of the hazelnut aroma might enhance the appeal of certain food products and perhaps increase consumer's consumption of the product. In addition, if a company is able to propose synthetic pathways that require fairly inexpensive compounds, these compounds can serve as a replacement for the natural product so that the company may be able to economically minimize cost of production over time. Overall synthetic reaction scheme: (a Chemdraw or similar drawing of all three steps)Step 1 Synthetic transformation 1: (Chemdraw picture of first transformation) Experimental 1 (notes if this transformation is not exactly the one reported in literature (e.g. on a different scale) and how it was modified): Starting material, 2-phenylpropene: 0.565 g/ 0.6 ml, 0.0047478 mols KBr: 0.704 g, 0.0071832 mols CH3CN: 23.7 ml/0.216 g, 0.0052668 mols NaOCl: 0.324 ml, 0.00527 mols Buffer: 23.7 ml (0.5 M KH2PO4) Na2SO3: 1 g Ethyl acetate: 40 ml Expected yield: 89 % 0.578 g Safety, disposal and green issues 1: KBr goes in base disposal; CH3CN is organic solvent NaOCl: Irritant Na2SO3: Keep away from acid, contact with acid liberates toxic gasStep 2 Synthetic transformation 2: (Chemdraw picture of second transformation) Experimental 2 (notes if this transformation is not exactly the one reported in literature (e.g. on a different scale) and how it was modified): Compound B, 2-methyl-2-phenyloxirane: 0.578 g, 0.00431 mols C2H5OΑBF3: 0.021 g, 0.000189 mols Diethyl ether: 1.5 ml Expected yield: 90% yield 0.524 g Safety, disposal and green issues 2: C2H5OΑBF3: corrosive, reacts violently with water, toxic by inhalation, causes burns Diethyl ether: EXTREMELY flammable and very harmfulStep 3 Synthetic transformation 3: (Chemdraw picture of third transformation) Experimental 3 Compound C, 2-Phenylpropanal: 0.524 g, 0.003879 mols Methanol: 0.786 ml, 0.786 mols H2SO4 : 0.419 ml, 0.00786 mols Expected yield: 71.9 % 1 g Safety, disposal and green issues 3: Methanol: highly toxic, flammableOverall budget: Chemical Supplier Cost Amt. Needed Total C2H5O*BF3 Sigma-Aldrich 0.183/g 0.000189 mol (.021g) $0.0038 NaOCl Sigma-Aldrich $.0968/ml 0.00527 mol (0.324 ml) $0.0314 2-phenylpropene Sigma-Aldrich $0.25/g 0.0047478 mol (0.565 g) $0.141 Diethylether Sigma-Aldrich $0.276/ml 1.5ml $0.414 Na2SO4 Sigma-Aldrich $0.167/g 1 g $0.167 Total costs per synthesis: __$0.77___________ References (include at least two different sources for your experimentals): H ek, J.; Ka r, P.; rven L. Res. Chem. Intermed. 2002, 28, 551-559. Karame, I.; Tommasino, M. L.; Lemaire, M. Tetrahedron Lett. 2003, 44, 7687-7689. Klawonn, M.; Bhor, S.; Mehltretter, G.; D ler, C.; Fischer, C.; Beller, M. Advanced Syn. & Catalysis. 2003, 345, 389-392. Tse, M. K.; Klawonn, M.; Bhor, S.; D ber, G. A.; Hugl, H.; M erlein, W.; Beller, M. Org. Lett. 2005, 7, 987-990. Sugai, Saburo; Kodama, Takashi; Akaboshi, Sanya; Ikegami, Shiro. Chem. Pharm. Bull. 1984, 32, 99-105. Shimizu, K.; Hayashi, E.; Hatamachi, T.; Kodama, T.; Kitayama, Y. Tetra. Lett. 2004, 45,
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