Researcher

Khalid Mirza

Objective

To determine the solubility of phenanthrene-9-carboxaldehyde, phenylacetic acid and the Ugi product UCExp176C in ethyl acetate.

Procedure

Solutions of phenanthrene-9-carboxaldehyde, phenylacetic acid and the Ugi product UCExp176C were prepared in ethylacetate and left in a temperature control bath at 40C for an hour and half. The temperature was then reduced to 25C and the samples were left to equlibrate for another hour. They were then centrifuged and HNMR of the supernatant obtained was used to assess their solubility by the SAMS method.

Results

Spreadsheet ONSCExp165-i


Discussion

Predicted solubility for the compounds match very closely to measured solubility.
Based on predictions made and the promising results from this experiment, there is a real good chance for ethyl acetate to over take methanol as a solvent of choice for the Ugi reactions involving phenanthrene-9-carboxaldehyde and phenylacetic acid
Self note: Addition of triethylamine to a solution of a dipeptide in ethyl acetate increases its solubility [Ref 9]
Compound
predicted solublity (M) *
measured solubility (M)
phenanthrene-9-carboxaldehyde
0.37
0.44
phenylacetic acid
3.33
3.98
Ugi product 176C (UC)
0.00
0.01
Table ONS165-i: For predicted solubility* refer to the solubility book

Conclusion

Solubility of phenanthrene-9-carboxaldehyde, phenylacetic acid and the Ugi product 176C (UC) has been determined by the SAMS method.

Log


2010-03-08
14:20 Powered on the thermostated water/glycol bath and set it to 40C
14:50 Made-up a solution of phenanthrene-9-carboxaldehyde, phenylacetic acid and the Ugi product UCExp176C in ethyl acetate in a three half dram vials. Made sure some solute remained undissolved even after vortexing the solution for 1min at room temp. The vial were labeled, the aldehyde solution 165-1, acid solution 165-2 and the Ugi product solution 165-3
15:00 Temp of the water/glycol bath was recorded at 40C
15:05 After parafilming the screw cap vials, placed them in to the water bath at 40C
15:45 Changed the temperature setting on the water bath to 25C.
16:10 Temperature of the bath was recorded at 25C
16:50 Removed the vials from the bath, obtained a picture of them with solid in them and centrifuged the vials.
17:00 Prepared three one dram vials with DMSO-d6 (750uL) in each and labeled them 165-1A, 165-2A and 165-3A
17:10 Pipetted out approximately 300uL supernatant from vials 165-1 in to 165-1A , 165-2 in to 165-2A, 165-3 in to 165-3A. Vortexed the resulting solutions. Transferred the solutions in to dry NMR tubes.
18:00 Obtained HNMR of the solutions.

References

  1. Solubility of Phenylacetic acid, p-Hydroxyphenylacetic Acid, p-Aminophenylacetic Acid, p-Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents; Sandra Gracin and, Åke C. Rasmuson; Journal of Chemical & Engineering Data 2002 47 (6), 1379-1383; http://dx.doi.org/10.1021/je0255170
  2. Solubility of phenylacetic acid in organic solvents; http://old.oru.edu/cccda/sl/solubility/allsolvents.php?solute=phenylacetic%2520acid
  3. Solubility of phenylacetic acid in ethyl acetate; http://old.oru.edu/cccda/sl/solubility/ugidata.php?solute=phenylacetic+acid&solvent=ethyl+acetate
  4. Solubility of the Ugi product 176C (UC) in organic solvents; http://old.oru.edu/cccda/sl/solubility/allsolvents.php?solute=Ugi+product+176C+%2528UC%2529
  5. Solubility of the Ugi product 176C (UC) in ethyl acetate; http://old.oru.edu/cccda/sl/solubility/ugidata.php?solute=Ugi%20product%20176C%20%28UC%29&solvent=ethyl+acetate
  6. Solubility of 9-phenanthrenecarboxaldehyde in organic solvents; http://old.oru.edu/cccda/sl/solubility/allsolvents.php?solute=phenanthrene-9-carboxaldehyde
  7. Solubility of 9-phenanthrenecarboxaldehyde in ethyl acetate; http://old.oru.edu/cccda/sl/solubility/ugidata.php?solute=phenanthrene-9-carboxaldehyde&solvent=ethyl+acetate
  8. Solubility of organic compounds in ethyl acetate; http://old.oru.edu/cccda/sl/chemspace/cs2.php?solvent=ethyl%20acetate
  9. A Study of Dipeptide Synthesis Catalyzed by Protease in Organic Solvent; Xue-Zhang, Songmin Chen, Xu Wang, et al.; Enzyme Engineering ; Volume 750 (XII), 24 - 29; http://dx.doi.org/10.1111/j.1749-6632.1995.tb19920.x