Exp271

=Researcher= Evan Curtin =Objective= To synthesize benzalaniline at 2M in trifluoroethanol(1), n-hexane(2) and isopropanol (3) =Procedure= Benzaldehyde (50mmol, 5.306g) was reacted with aniline (50mmol, 4.656g) at 2M concentration in trifluoroethanol (20.351g) and isopropanol (12.150g). Precipitate from the isopropanol mixture was filtered using a buchner funnel, washed with ethanol and characterized by HNMR. The trifluoroethanol did not form a precipitate and the solution was analyzed by HNMR. =Results= UC-EXP271 Plan Sheet media type="custom" key="10211311" media type="custom" key="10211321" =Discussion= =Conclusion= Benzalaniline was successfully synthesized in isopropanol, however it is too soluble to precipitate out of trifluoroethanol and the starting materials are not soluble enough to dissolve in hexane. =Log=
 * Characterization of 3A:**
 * Reaction Mixture for 1:**
 * 1)** Imine did form in trifluoroethanol, however there was not enough to form a precipitate. The solubility of benzalaniline in trifluoroethanol is 3.682, which explains why the product never precipitated.
 * 2)** Aniline is not soluble enough in n-hexane to be able to run the reaction at high concentrations.
 * 3)** The product precipitated in isopropanol and had a yield of 62%. The solubility for benzalaniline in isopropanol at 0C is 0.3M. Running the reaction at 2M would result in an optimal yield of 85%. Human error is likely to blame for the discrepancy.

2011-08-01
15:08 - Weighed reactants. Weighed 50 mmol of each reactant as well as enough solvent to run the reaction at 2M trifluoroethanol (20.3527g), n-hexane (10.3841g), and isopropanol (12.1479g). Used roughly half of each solvent to dissolve the starting materials. However, Aniline did not mix with n-hexane, even after roughly quadrupling the volume with hexane. 15:09 - Mixed solutions of benzaldehyde and aniline from in a 250mL erlenmeyer flask with both trifluoroethanol and isopropanol as solvents. Added magnetic stirring rod, parafilmed and set on a stirring plate. 15:50 - Precipitate formed in 3, removed from stirring plate and put in an ice/water bath. 15:58 - Filtered 3, put solid in 2 separate vials, each with punctured caps, in a desiccator under high vacuum. 17:05 - 1 Still has no precipitate, left on stirring plate. 2011-08-02 16:42 - Re moved sample 3 from desiccator (now called 3A), weighed. Mass is 5.5828g. 17:02 - Added CDCl3 to a small amount of 3A, put in NMR tube. 17:14 - Took HNMR of sample 3A using 500MHz varian NMR.