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

III. Calculations

Part 1
Theoretical Yield

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

Rf Values
Starting material = 4.0/5.5 = 0.73
Final product = 1.7/5.5 = 0.31
Part 2
Theoretical Yield

3) (1.00 g ethyl vanillyl alcohol x 182.2 g methyl diantilis) / (154.16 g ethyl vanillyl alcohol) = 1.182 g methyl diantilis 4) (0.5 g NaHCO3 x 182.2 g methyl diantilis) / (84.007 g NaHCO3) = 1.084 g methyl diantilis

Percent Yield = (0.812 g / 1.084 g) x 100 = 74.9%

Rf Values
Starting material = 1.9/5.4 = 0.35
Final product = 3.6/5.4 = 0.67

Starting material = 1.9/4.9 = 0.38
Methyl Diantilis = 2.9/4.9 = 0.59

IV. Results

Part 1
Initial Mass Ethyl Vanillin = 1.621 g
Initial Mass NaBH4 = 0.308 g
Final Mass Ethyl Vanillyl Alcohol = 1.03 g

When NaOH was added to ethyl vanillin, solution turned yellow in color and after refluxing, it remained yellow. While adding 6 mL of HCl to the solution, it foamed vigorously and turned to a cloudy, white color. It took about 6mL of 2.5M HCL to get an acidic result on the PH A paper. The final product, ethyl vanillyl alcohol was a bluish-green powder.

IR spec of the final product revealed a broad, but weak OH peak.

Part 2
Initial Mass Amberlyst-15 = 1.090 g
Initial Mass NaHCO3 = 0.496 g
Final Mass Methyl Diantilis =