Optimisation of ethyl(2-phthalimidoethoxy)acetate synthesis with the aid of DOE

Organic Process Research and Development

Volumn 9, Issue 1, 2005, Pages 18-22

  Synoradzki, Ludwik ^a   Jańczewski, Dominik ^a   Włostowski, Marek ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE;

ALKYNYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FACTORIAL ANALYSIS; PHASE SEPARATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13844298043     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op030029y     Document Type: Article

References (24)

1. For example see: (a) Adler, Yu. P.; Markowa, E. V.; Granovsky, Yu. V. The Design of Experiments to Find Optimal Conditions; Mir Publishers: Moscow, 1975. (b) Achnazarowa, S. Ł.; Kafarow, W. W. Optymalizacja eksperymentu w chemii i technologii chemicznej; WNT: Warszawa, 1982. (c) Morgan, E. Chemometrics: Experimental Design; J. Wiley & Sons: Chichester, 1991. (d) Jańczewski, D.; Różycki, C.; Synoradzki, L. Projektowanie procesów technologicznych cz. 2; OWPW: Warszawa, 2001. (e) Carlson, R. Design and Optimisation in Organic Synthesis; Elsevier Science: Amsterdam, 1992.
2. For example see: (a) Adler, Yu. P.; Markowa, E. V.; Granovsky, Yu. V. The Design of Experiments to Find Optimal Conditions; Mir Publishers: Moscow, 1975. (b) Achnazarowa, S. Ł.; Kafarow, W. W. Optymalizacja eksperymentu w chemii i technologii chemicznej; WNT: Warszawa, 1982. (c) Morgan, E. Chemometrics: Experimental Design; J. Wiley & Sons: Chichester, 1991. (d) Jańczewski, D.; Różycki, C.; Synoradzki, L. Projektowanie procesów technologicznych cz. 2; OWPW: Warszawa, 2001. (e) Carlson, R. Design and Optimisation in Organic Synthesis; Elsevier Science: Amsterdam, 1992.
3. For example see: (a) Adler, Yu. P.; Markowa, E. V.; Granovsky, Yu. V. The Design of Experiments to Find Optimal Conditions; Mir Publishers: Moscow, 1975. (b) Achnazarowa, S. Ł.; Kafarow, W. W. Optymalizacja eksperymentu w chemii i technologii chemicznej; WNT: Warszawa, 1982. (c) Morgan, E. Chemometrics: Experimental Design; J. Wiley & Sons: Chichester, 1991. (d) Jańczewski, D.; Różycki, C.; Synoradzki, L. Projektowanie procesów technologicznych cz. 2; OWPW: Warszawa, 2001. (e) Carlson, R. Design and Optimisation in Organic Synthesis; Elsevier Science: Amsterdam, 1992.
4. For example see: (a) Adler, Yu. P.; Markowa, E. V.; Granovsky, Yu. V. The Design of Experiments to Find Optimal Conditions; Mir Publishers: Moscow, 1975. (b) Achnazarowa, S. Ł.; Kafarow, W. W. Optymalizacja eksperymentu w chemii i technologii chemicznej; WNT: Warszawa, 1982. (c) Morgan, E. Chemometrics: Experimental Design; J. Wiley & Sons: Chichester, 1991. (d) Jańczewski, D.; Różycki, C.; Synoradzki, L. Projektowanie procesów technologicznych cz. 2; OWPW: Warszawa, 2001. (e) Carlson, R. Design and Optimisation in Organic Synthesis; Elsevier Science: Amsterdam, 1992.
5. For example see: (a) Adler, Yu. P.; Markowa, E. V.; Granovsky, Yu. V. The Design of Experiments to Find Optimal Conditions; Mir Publishers: Moscow, 1975. (b) Achnazarowa, S. Ł.; Kafarow, W. W. Optymalizacja eksperymentu w chemii i technologii chemicznej; WNT: Warszawa, 1982. (c) Morgan, E. Chemometrics: Experimental Design; J. Wiley & Sons: Chichester, 1991. (d) Jańczewski, D.; Różycki, C.; Synoradzki, L. Projektowanie procesów technologicznych cz. 2; OWPW: Warszawa, 2001. (e) Carlson, R. Design and Optimisation in Organic Synthesis; Elsevier Science: Amsterdam, 1992.
6. (a) Jańczewski, D.; Synoradzki, L.; Włostowski, M. 45th Conference of The Polish Chemical Society; Kraków, 2003; Vol. 1, p 156. (b) Włostowski, M.; Jańczewski, D.; Synoradzki L. The Rearrangement of Anions Generated from some N-Substituted Activated Phthalimides. Manuscript in preparation.
7. (a) Jańczewski, D.; Synoradzki, L.; Włostowski, M. 45th Conference of The Polish Chemical Society; Kraków, 2003; Vol. 1, p 156. (b) Włostowski, M.; Jańczewski, D.; Synoradzki L. The Rearrangement of Anions Generated from some N-Substituted Activated Phthalimides. Manuscript in preparation.
8. For example see: (a) Henze, H. R.; Rogers, G. B. J. Am. Chem. Soc. 1939, 61, 433. (b) Mariella, R. P.; Belcher, E. P. J. Am. Chem. Soc. 1952, 74, 4049. (c) Micheau, J. C.; Lattes, A. Bull. Soc. Chim. Fr. 1970, 4018. (d) Field, L.; Carlile, C. G. J. Org. Chem. 1961, 26, 3170. (e) Gorina, N. Yu.; Zakharowa, N. I.; Filipowa, T. M.; Suchkova, I. G.; Samokhvalov, G. I. J. Org. Chem. U.S.S.R. 1991, 27, 1617.
9. For example see: (a) Henze, H. R.; Rogers, G. B. J. Am. Chem. Soc. 1939, 61, 433. (b) Mariella, R. P.; Belcher, E. P. J. Am. Chem. Soc. 1952, 74, 4049. (c) Micheau, J. C.; Lattes, A. Bull. Soc. Chim. Fr. 1970, 4018. (d) Field, L.; Carlile, C. G. J. Org. Chem. 1961, 26, 3170. (e) Gorina, N. Yu.; Zakharowa, N. I.; Filipowa, T. M.; Suchkova, I. G.; Samokhvalov, G. I. J. Org. Chem. U.S.S.R. 1991, 27, 1617.
10. For example see: (a) Henze, H. R.; Rogers, G. B. J. Am. Chem. Soc. 1939, 61, 433. (b) Mariella, R. P.; Belcher, E. P. J. Am. Chem. Soc. 1952, 74, 4049. (c) Micheau, J. C.; Lattes, A. Bull. Soc. Chim. Fr. 1970, 4018. (d) Field, L.; Carlile, C. G. J. Org. Chem. 1961, 26, 3170. (e) Gorina, N. Yu.; Zakharowa, N. I.; Filipowa, T. M.; Suchkova, I. G.; Samokhvalov, G. I. J. Org. Chem. U.S.S.R. 1991, 27, 1617.
11. For example see: (a) Henze, H. R.; Rogers, G. B. J. Am. Chem. Soc. 1939, 61, 433. (b) Mariella, R. P.; Belcher, E. P. J. Am. Chem. Soc. 1952, 74, 4049. (c) Micheau, J. C.; Lattes, A. Bull. Soc. Chim. Fr. 1970, 4018. (d) Field, L.; Carlile, C. G. J. Org. Chem. 1961, 26, 3170. (e) Gorina, N. Yu.; Zakharowa, N. I.; Filipowa, T. M.; Suchkova, I. G.; Samokhvalov, G. I. J. Org. Chem. U.S.S.R. 1991, 27, 1617.
12. For example see: (a) Henze, H. R.; Rogers, G. B. J. Am. Chem. Soc. 1939, 61, 433. (b) Mariella, R. P.; Belcher, E. P. J. Am. Chem. Soc. 1952, 74, 4049. (c) Micheau, J. C.; Lattes, A. Bull. Soc. Chim. Fr. 1970, 4018. (d) Field, L.; Carlile, C. G. J. Org. Chem. 1961, 26, 3170. (e) Gorina, N. Yu.; Zakharowa, N. I.; Filipowa, T. M.; Suchkova, I. G.; Samokhvalov, G. I. J. Org. Chem. U.S.S.R. 1991, 27, 1617.
13. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
14. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
15. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
16. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
17. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
18. For example see: (a) Portlock, D. E.; Ghost, A. C.; Schwarzel W. E. J. Heterocycl. Chem. 1976, 13, 781. (b) Davis H. A.; Brown, R. K. Can. J. Chem. 1971, 49, 2563. (c) Leggetter, B. E.; Brown, R. K. Can. J. Chem. 1964, 42, 990. (d) Lown, J. W.; Koganty, R. R.; Joshua A. V. J. Org. Chem. 1982, 47, 2027. (e) Liu, Y.-Y.; Thom, E.; Liebman, A. A. Can. J. Chem. 1978, 56, 2853. (f) Rubini, E.; Gilon, C.; Selinger, Z.; Chorev, M. Tetrahedron 1986, 42, 6039.
19. Jańczewski, D.; Synoradzki, L.; Włostowski, M. Synlett 2003, 3, 420.
20. (a) Yu, R. H.; Schultze, L. M.; Rohloff, J. C.; Dudzinski, P. W.; Kelly, D. E. Org. Process Res. Dev. 1999, 3, 53.
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22. De Wall, G. Chem. Eng. News 1982, 60, 5 and 43.
23. All calculations were done with MS Excel.
24. March, J. Advanced Organic Chemistry, 3rd ed.; J. Wiley & Sons: New York, 1985.