Exp274

=Researcher= Evan Curtin =Objective= To synthesize benzalaniline in methanol and recrystallize in ethanol to test yield predictions. =Procedure= =Results= Plan Sheet (Includes recrystallization) media type="custom" key="10209365" media type="custom" key="10229443"
 * Characterization of 1A:**
 * Characterization of 1B:**

=Discussion= 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. =Conclusion= Benzalaniline was synthesized with a yield of 64.6% and recrystallized with a yield of 71.1%. =Log=

2011-08-11
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.

2011-08-12
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.

2011-08-18
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.

2011-08-19
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.