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2142726772
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note
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Dodecylbenzenesulfonic acid (soft type) was purchased from Tokyo Kasei Kogyo Co., Ltd. This is a mixture of linear alkylbenzenesulfonic acids. Its molecular weight was regarded as 326.50.
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55
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2142678777
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note
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Stirring (usually 1400 rpm) of the reaction mixture was not very important to keep it an emulsion system. Without stirring, large, visible droplets were formed, but the aqueous phase was still a white turbid solution (the yield of 3-phenylpropyl laurate is 58% after 24 h at 40°C without stirring). Cf. ref 12i.
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57
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2142792525
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note
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For a typical experimental procedure, see the Supporting Information.
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58
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84942048668
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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For examples of selective esterification of nonconjugated carboxylic acids over aromatic or conjugated carboxylic acids. see: (a) Blossey, E. C.; Turner, L. M.; Neekers, D. C. Tetrahedron Lett. 1973, 1823. (b) Bertin, J.; Kagan, H. B.; Luche, J.-L.; Setton, R. J. Am. Chem. Soc. 1974, 96, 8113. (c) Rehn, D.; Ugi, I. J. Chem. Res. Synop. 1977, 119. (d) Banerjee, A.; Sengupta, S.; Adak, M. M.; Banerjee, G. C. J. Org. Chem. 1983, 48, 3106. (e) Matsumoto, I. Jpn. Kokai Tokkyo Koho JP 59 152,347 [84 152,347] (Cl. C07C67/08), Chem. Abstr. 1985, 102, 5952w. (f) Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 3473. (g) Ram, R. N.; Charles, I. Tetrahedron 1997, 53, 7335. (h) Rodríguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563. (i) Lee, A. S.-Y.; Yang, H.-C.; Su, F.-Y. Tetrahedron Lett. 2001, 42, 301.
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