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The Synthesis of Benzophenone-3,5-Diacid Chloride for the Double Capping of Beta-Cyclodextrin

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The Synthesis of Benzophenone-3,5-Diacid Chloride for the Double Capping of Beta-Cyclodextrin W&M ScholarWorks Dissertations, Theses, and Masters Projects Theses, Dissertations, & Master Projects 1997 The Synthesis of Benzophenone-3,5-Diacid Chloride for the Double Capping of beta-Cyclodextrin Clyde Wesley Eargle College of William & Mary - Arts & Sciences Follow this and additional works at: https://scholarworks.wm.edu/etd Part of the Organic Chemistry Commons Recommended Citation Eargle, Clyde Wesley, "The Synthesis of Benzophenone-3,5-Diacid Chloride for the Double Capping of beta- Cyclodextrin" (1997). Dissertations, Theses, and Masters Projects. Paper 1539626104. https://dx.doi.org/doi:10.21220/s2-en0f-nh60 This Thesis is brought to you for free and open access by the Theses, Dissertations, & Master Projects at W&M ScholarWorks. It has been accepted for inclusion in Dissertations, Theses, and Masters Projects by an authorized administrator of W&M ScholarWorks. For more information, please contact [email protected]. The Synthesis of Benzophenone-3,5-Diacid Chloride for the Double Capping of p-Cyclodextrin A Thesis Presented to The Faculty of the Chemistry Department The College of William and Mary in Virginia In Partial Fulfillment of the Requirements for the Degree of Master of Arts by C. Wesley Eargle 1997 APPROVAL SHEET This thesis is submitted in partial fulfillment of the requirements for the degree of Master of Arts Approved, April 1997 Gary W. Rice, Ph.D. Robert J. Hinkle, Ph.D. ii DEDICATION This project would have never come as far as it has without the guidance and support of many people, far too many to list on a single page. The author would like to single out three individuals who have, in one way or another, pushed me towards this final goal. This thesis is dedicated to the memory of my brother, Charles Parham Eargle, jr., who never got to appreciate the good times that should have been. This thesis is also dedicated to the memory of my grandfather, Clyde Woodward Rutland, for providing the example that I should hope to follow for the rest of my life. This thesis is also dedicated in honor of my best friend, J.P. Northrop, whose constant support and encouragement allowed me to get through the tough times. Without these people in my life, this thesis would have never come to fruition. TABLE OF CONTENTS DEDICATION................................................................................ iii ACKNOWLEDGEMENTS.......................................................... v LIST OF TABLES.......................... vi LIST OF FIGURES............................................................................ vii ABSTRACT .............................................................................................................ix INTRODUCTION.....................................................................................................................2 BACKGROUND......................... .:.................................................... 6 * * CyClodextrins .................................................................................................................6 Inclusion Complexes .................. 9 Capping..................... 12 Photochemistry. ........................ 17 Previous Synthetic Pathways ......................... ............. ............ ................................ 21 MATERIALS AND METHODS....... ............................................................................ 24 1 -Bromo-3,5-dimethylbenzene............................................................ ......................26 N,N-Diethylbenzamide ..............................................................................................27 3.5-Dimethylbenzophenone (Lithiation Pathway) ...................................................28 3.5-Dimethylbenzophenone (Grignard Pathway) ....................................................29 Benzophenone-3,5-dicarboxylic acid ...................................... ................................. 30 Benzophenone-3,5-dicarboxylic acid chloride .................................. 30 6A, 6B, 6A, 6B -(Benzophenone-3,5-diacid)2-/?-cyclodextrin ................. .................. 31 RESULTS AND DISCUSSION........................................................................................... 32 CONCLUSION ............................................................................................................42 APPENDICES........................ ...............................................................................................43 Appendix I: !H and 13C NMR Spectra ......................................................................43 Appendix II: Internet NMR Predictions .................... ..............................................53 Appendix HI: PC Model Bali and Stick Structures ................. ............................... 63 REFERENCES....................................................................................................................... 65 VITA 67 ACKNOWLEDGMENTS The author wishes to express his appreciation to Professor Christopher J. Abelt for his patient guidance and encouragement throughout the investigation and in the preparation of this thesis. The writer also indebted to Professors Gary W. Rice and Robert J. Hinkle for their help in critiquing and offering suggestions for this manuscript, and to Professors W. Gary Hollis and Jonathan Touster for their inspiration and tireless patience during my undergraduate studies. v LIST OF TABLES Table Page 1. Molecular Modeling Data for Benzopinacol Capped /?-cyclodextrin ..................40 vi LIST OF FIGURES Figure Page 1. Structures of a and y -cyclodextrins..... ................ ......................................6 2. Dimensions of a - , j]-, and y -cyclodextrins ............ 7 3. Faces of Cyclodextrins .......................... 8 4. Hydrophobic Effect .............................................................................................................11 5. Breslow’s “Flexible Cap” ........................................................................................13 6. First True Cyclodextrin Cap ............................................................................................... 14 7. Loopers Walk vs Oligomerization. .................................................................................... 14 8. AB, AC and AD Caps on /?-Cyclodextrin. ....................... 15 9. Tabushi’s Regiospecific AB, AC and AD Caps ............................................. 16 10. Benzopinacol Formation ................... 19 11. Three Major Pinacol Products .................................................................................. 20 12. High Intensity Radiation Induced Radical-Radical Reactions ...................................... 21 13. Proposed Acetylisophthalic Acid Synthesis ....................................................... 22 14. Synthesis of 5-Cyano-l,3-Isophthalic Acid ............... 22 15. Synthesis of Benzophenone-3,5-Dicarboxylic Acid ...................................................... 23 16. Synthesis of l-Bromo-3,5-Dimethylbenzophenone ................... 33 17. Synthesis of N,N-Diethylbenzamide ................................................................................33 18. Synthesis of 3,5-Dimethylbenzophenone (Lithiation Pathway) .................................... 34 19. Synthesis of 3,5-Dimethylbenzophenone (Grignard Pathway) ..................................... 35 20. Mechanism for the Oxidation of Methyl Groups to the Corresponding Acids ............36 21. Synthesis of Benzophenone-3,5-Diacid Chloride ...........................................................38 22. ’H NMR Spectrum of l-Bromo-3,5-dimethylbenzene ...................................... 43 23. 13C NMR Spectrum of l-Bromo-3,5-dimethylbenzene ................... 44 24. 'H-NMR Spectrum of N,N-Diethylbenzamide ........................ 45 25. 13C NMR Spectrum of N,N-Diethylbenzamide ..............................................................46 26. ‘H NMR Spectrum of 3,5-Dimethylbenzophenone (Lithiation Pathway) ............... ....47 27. ‘H NMR Spectrum of 3,5-Dimethylbenzophenone (Grignard Pathway) ..................... 48 28.13C NMR Spectrum of 3,5-Dimethylbenzophenone (Grignard Pathway) .................... 49 29. 'HNMR Spectrum of Benzophenone-3,5-dicarboxylic acid .........................................50 30. 13C NMR Spectrum of Benzophenone-3,5-dicarboxylic acid ............................. ...51 31. ‘H NMR Spectrum of Benzophenone-3,5-dicarboxylic acid chloride ..........................52 32. Predicted 'H NMR Spectrum of l-Bromo-3,5-dimethylbenzene .................................. 53 33. Predicted ,3C NMR Spectrum ofl-Bromo-3,5-dimethylbenzene .................................. 54 34. Predicted !H NMR Spectrum of N,N-Diethylbenzamide ...............................................55 35. Predicted 13C NMR Spectrum ofN,N-Diethylbenzamide ............................................. .56 36. Predicted *H NMR Spectrum of 3,5-Dimethylbenzophenone..!.... ................................ 57 37. Predicted 13C NMR Spectrum of 3,5-Dimethylbenzophenone .......................................58 38. Predicted’H NMR Spectrum of Benzophenone-3,5-dicarboxylic acid... .....................59 39. Predicted 13C NMR Spectrum of Benzophenone-3,5-dicarboxylic acid.. .................... 60 40. Predicted *H NMR Spectrum of Benzophenone-3,5-dicarboxylic acid chloride 61 vii Figure Page 41. Predicted 13C NMR Spectrum of Benzophenone-3,5-dicarboxylic acid chloride 62 42. Ball and Stick Structure of ABCD3 — Side View .........................................................63
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