Chalcone - Green Synthesis and Hydrogenation of a...

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Green Synthesis and Hydrogenation of a Di-Substitution Chalcone Purpose: The purpose of this experiment was to synthesize Chalcone 1 with an aldol condensation reaction between para-chlorobenzaldehyde and para-methoxyacetophenone. The crude Chalcone 1 was purified by recrystallization, its identity and purity was confirmed by analyzing the melting point, mass spectrum, Infrared spectroscopy and 1 H NMR spectroscopy. The purified Chalcone 1 was hydrogenated with methanol, ammonium formate and palladium to form a product of unknown identity. The structure of the product could be predicted by analyzing the melting point, IR, mass spectrum and 1 H NMR of the unknown product. Reaction: Aldol Condensation Hydrogenation Mechanism: Procedure:
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The procedure followed was as is described in “Laboratory Manual for Organic Chemistry 2311”, Eighth Edition, Jane E. Wissinger, Cengage Learning, Mason, Ohio, 2010, pp. 105-110. Reagent/Product Table for Aldol Condensation: p-chloro benzaldehyde p-methoxy acetophenone Ethano l Sodium Hydroxid e Chalcone 1 1 Molecular Mass (g/mol) 140.57 150.17 46.07 40 272.73 1 Mass (g) 0.492 0.52 x 0.41 0.83 1 Milli Moles 3.50 3.46 x 10.25 3.04 1 Volume (mL) 0.41 x x 0.19 x Density (g/cm 3 ) 1.196 x 0.789 2.13 x Boiling Point (°C) 214 152 78 1390 x Melting Point (°C) 46 36 -114 318 2 130-131 ( 1 ) This information was collected during the experiment ( 2 ) Palleros, D.R . J. Chem. Educ . 2004, 81, 1345-1347 All other information was collected from Results and Observation for Experiment 1 (Synthesis): Para-chloro benzaldehyde and p-methoxyacetophenone are white crystals and dissolve in ethanol. 4 Sodium Hydroxide pellets were used, which were crushed and added to the solution. The mixture turned pale yellow initially then white precipitate forms. Few mls of water is added and light custard yellow froth forms. The mixture was heated by keeping temperature between 60-65°C for 30 minutes, however for a few minutes the temperature did increase to 69°C. The solution is filtered to give pale custard yellow powder, but after washing with water white powder is left. The crude mass was taken then the crystals were dissolved in ethanol to give yellow liquid. Recrystallized crystals were flaky, shiny, transparent and cream coloured. The mass was recorded and melting point taken. Yield and Properties of Chalcone 1 Theoretica l Yield Actua l Yield % Yield Corrected %Yield Melting Point (°C) Appearance Crude 0.94 g 1.35 g 143.7 % x x white powder Pure 0.94 g 0.83 g 88.3% 88.1% 129.1 - 131.4 Flaky, shiny, transparent and cream coloured Literature Melting Point 2 130-131
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( 2 ) Palleros, D.R . J. Chem. Educ
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