To Synthesize a Fragrance Used Commercially in Two Steps by Using a Chemoselective Reduction Reaction, and a Polymer-Supported Reaction.
What’s That Smell?
Due Date/Submission Date: 02/17/2014 I. Purpose
To synthesize a fragrance used commercially in two steps by using a chemoselective reduction reaction, and a polymer-supported reaction.
II. Reaction Equations and Mechanisms
1) (1.62 g ethyl vanillin x 154.16 g ethyl vanillyl alcohol) / (166.18 g ethyl vanillin) = 1.503 g ethyl vanillyl alcohol 2) (0.3 g NaBH4 x 154.16 g ethyl vanillyl alcohol) / (37.83 g NaBH4) = 1.223 g ethyl vanillyl alcohol
Percent Yield = (1.03 g / 1.223 g) x 100 = 84.2%
Melting Point Range ( ̊C): 83.9, 84.4, 85.0
Melting Point Average ( ̊C): 84.43
Starting material = 4.0/5.5 = 0.73
Final product =
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These differences show that the product material is different from the starting material and is more pure as it has more O-H that are more defined. 4. Our melting point range and average (84.43) for the product, ethyl vanillin alcohol, was a lot lower than ethyl vanillin alcohol’s actual melting point (112). This suggests our product is not very pure and contains a lot of impurities. 5. The synthetic procedure for chemo selectively reducing an aldehyde functional group in the presence of an ether functional group was pretty successful and very effective. Both IR spectrums show the presence of C-O bonds of the ether group indicating that it remained from the starting material to the product. The only difference between the two materials as indicated from the IR spectrum is the removal of an aldehyde group from the starting material and the addition of an alcohol group in the product material, making this an effective chemo selective reaction. 6. Our percent yield for methyl diantilis is low (74.9%). This is due to the fact that we forgot to add the sodium bicarbonate to the flask, so we had to repeat some steps and might have added an excess of methanol as we had to repeat the gravity filtration twice due to this mistake. 7. The TLC plate results showed to separate spots that traveled different distances, one spot for ethyl vanillin alcohol (starting) and one spot for methyl diantilis (product). The product was more polar as indicated by