UCexp268scheme_2.png

Researcher

Evan Curtin

Objective

To synthesize an imine from vanillin and aniline in order to collect solubility data.

Procedure

Results

Exp268 Plan Sheet
Characterization of 1A:



Characterization of 1B:


Characterization of 1C:

Discussion

Conclusion

Log

2011-06-20

14:15 - Made a solution of 7.6143g vanillin and 31.0074g ethanol. Measured 4.6578g aniline in a vial.
14:18 - Added vanillin/ethanol solution to a 250mL erlenmeyer flask, slowly added aniline to the solution. Covered in parafilm and set on magnetic stirring plate. Solution is clear.
14:44 - Mixture is bright yellow and cloudy, chilled with water and ice.
14:51 - Filtered the mixture using a bΓΌchner funnel and house vacuum. Put the mixture in a vial with cap (mass of vial and cap is 13.8520g). Punctured cap of vial and set in desiccator under high vacuum.

2011-06-21

14:10 - Removed sample from desiccator (1A). Made a solution of the product and CDCl3. Added solution to NMR tube.
14:30 - Took HNMR using 300MHz varian NMR (HNMR-1A).
15:30 - Took some sample in a melting point capillary, started heating.
15:31 - Temperature is 30C (the following entries are all for the temperature on the thermometer of the melting point apparatus)
15:32 - 37C
15:33 - 46C
15:34 - 65C
15:35 - 90C
15:36 - 100C
15:37 - 99C
15:38 - 95C
15:39 - 98C
15:40 - 102C
15:41 - 103C
15:42 - 102C
15:43 - 105C
15:44 - 112C
15:45 - 115C
15:46 - 114.5C
15:47 - 116C
15:48 - 122C
15:49 - 126C
15:50 - 128C
15:51 - 129C
15:52 - 132C
15:53 - 136C
15:54 - 138C
15:55 - 140C
15:56 - 142C
15:57 - 145C
15:58 - 147C
15:59 - 151C
[what is the melting point? JCB]

2011-06-22

12:11 - Put sample 1A into desiccator under high vacuum.
14:15 - Removed sample (now 1B) from desiccator.[report mass and add to sheet to get yield JCB]
14:20 - Added CDCl3 to some of the sample, transferred to NMR tube
14:34 - Took HNMR spectrum using 500MHz varian NMR (HNMR 1B).
14:52 - Put sample 1B into desiccator under high vacuum.

2011-06-23

13:47 - Removed sample (now 1C) from desiccator.
14:03 - Add CDCl3 to some of the sample, transferred to NMR tube.
14:25 - Took HNMR spectrum using varian 300MHz NMR (HNMR 1C).