Evan Curtin


To synthesize benzalaniline in methanol and recrystallize in ethanol to test yield predictions.



Plan Sheet (Includes recrystallization)
Characterization of 1A:

Characterization of 1B:


Expected yield for synthesis at 2M in methanol with one wash is 69%, consistent with the 64.6% obtained experimentally. The expected recrystallization yield was 89%, however the experimental yield was only 71.1%. The difference between the two could be a result of the solution not cooling to 0C, or error resulting in loss of some of the sample.


Benzalaniline was synthesized with a yield of 64.6% and recrystallized with a yield of 71.1%.



13:41 - Weighed 5.30209g benzaldehyde, 4.65289g aniline and 11.57g methanol. Added half of the methanol to benzaldehyde, and added the other half of the methanol to aniline.
13:47 - Mixed solutions of each reactant together in a 50mL erlenmeyer flask and covered with parafilm.
15:33 - Precipitate formed after sonication.
15:43 - Chilled the product and 11.57g methanol in a 0C ice/water bath.
16:05 - Filtered using a buchner funnel, washed the solid once with the chilled methanol.
16:36 - Put solid in two separate 3 dram push-cap vials, with punctured tops and placed in desiccator under high vacuum.
17:32 - Removed from desiccator.


9:23 - Took some of sample 1A, dissolved in CDCl3 and transferred to NMR tube.
9:32 - Took HNMR1 of 1A using 500MHz varian NMR.


11:22 - Added sample to desiccator under high vacuum.
12:58 - Removed from desiccator. Weighed. Mass is 5.8499g.
13:09 - Dissolved some of sample 1B in CDCl3 and transferred to NMR tube.
13:17 - Took HNMR1 of 1B using 300MHz varian NMR.


14:05 - Weighed 2.6099g benzalaniline and 3.4912g ethanol
14:16 - Heated on hot plate
14:20 - All of the sample dissolved. There are no layers present in the solution.
14:21 - Put solution in ice bath.
14:29 - Precipitate formed, filtered using a buchner funnel. Put in desiccator under high vacuum.
16:02 - Removed from desiccator. Weighed the sample. Mass is 1.8546g. Took some sample and mixed with CDCl3, transferred to NMR tube
16:45 - Took HNMR using 500MHz varian NMR.