What’s That Smell?
Due Date/Submission Date: 02/17/2014
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
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When the ethyl vanillyl alcohol was added to the brown Amberlyst-15 and methanol it dissolved immediately into a clear liquid. While we refluxed the solution there was no color change, the solution stayed clear. After gravity filtration the solution stayed clear. After roto vap, solution was a milky brown color.
IR spec data showed a weak OH peak as well as strong C—O stretches around 1200 cm-1.
V. Discussion Questions:
1. Our percent yield for alcohol was 84.2% which is average. We rushed through our vacuum filtration and probably did not let the solid dry long enough and might have not transferred all of the solid to the vacuum filtration from the beaker.
2. The TLC results showed two different spots that traveled different distances on the TLC plate, one for ethyl vanillin and one for ethyl vanillin alcohol which proves there is no evidence of the starting material in our final product. The product (ethyl vanillin alcohol) was more polar and interacted more with the solvent than our starting material (ethyl vanillin). This increase in polarity is due to the extra alcohol group in the ethyl vanillin alcohol and the smaller Rf value also indicates it is more polar and pure than the ethyl vanillin.
3. The IR spectrum of the starting material shows a medium/strong C-O bond at around 1500cm-1, also the starting material shows a strong C-H bond at around 3000cm-1 and another medium C-H bond at 2865cm-1 indicating an aldehyde group whereas the product does not. The IR spectrum of the product shows a two weak broad O-H peaks at around 3100-3350cm-1 indicating two alcohol groups whereas the product only shows one at around 3200cm-1 indicating only one alcohol group. 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...