Experiment #28-Borohydride Reduction of Vanillin to Vanillyl Alcohol

Experiment #28-Borohydride Reduction of Vanillin to Vanillyl Alcohol

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Lauren Margerum 4/30/2007 Borohydride Reduction of Vanillin to Vanillyl Alcohol Purpose: To adapt and modify an existing procedure for a similar synthesis, devise a procedure based upon the knowledge of the substrate, reagent, product, and the reaction involved. Also, invent a new way of synthesizing a compound wishing to be made. Chemistry: If the reaction solvent is an alcohol, the reaction mixture is usually concentrated by evaporating most of the alcohol. Water is then added and the product is extracted with a suitable solvent. In the following reaction, sodium borohyrdride is added to water and vanillin. This then yields vanillyl alcohol, boric acid, and sodium hydroxide. This can be seen in the following illustration: O OH O + O H 2 OH OH O + N a B H 4 + 4 4 4 H 3 B
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Unformatted text preview: O 3 + N a O H Vanillin Sodium Water Vanillyl Boric Sodium Borohydride Alcohol Acid Hydroxide Materials: Reagents: Selected Physical Properties: *Taken from Multiscale Operational Organic Chemistry by John W. Lehman *m.p. and b.p. are in C; d = decomposes 1 M.W. m.p. b.p. Vanillin 152.2 79 285 Sodium Borohydride 37.83 400d Vanillyl Alcohol 154.2 115 d Lauren Margerum 4/30/2007 Apparatus: Procedure: Results: Conclusion: After taking a melting point temperature, which was between 79 and 80 degrees Celsius, I hypothesize that my actual product was in fact Vanillin and not Vanillyl alcohol. Therefore, one is left to conclude that the procedure for this given experiment, did in fact not work. 2 Lauren Margerum 4/30/2007...
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Experiment #28-Borohydride Reduction of Vanillin to Vanillyl Alcohol

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