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Regioselective Direct Carboxylation of 2-Naphthol with Supercritical CO2 in the Presence of K2CO3

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DOI: 10.4236/ijoc.2013.33028    3,883 Downloads   5,877 Views  

ABSTRACT

A direct regioselective preparation of 2-hydroxynaphthalene-6-carboxylic acid, a useful industrial intermediate of aro-matic polyester from 2-naphthol was conducted by use of excess amount of K2CO3 (10-fold molar to 2-naphthol) under supercritical CO2 at 10 MPa and 473 K. The obtained yield under this condition was ca. 20 mol% to 2-naphthol. The further investigations may provide an alternative process to the conventional Kolbe-Schmitt reaction, because of no use of strong alkali and recoverability of K2CO3. Theoretical explanation about the regioselectivity was achieved by means of DFT calculations.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

S. Furukawa, K. Otokawa, O. Sasaki, K. Nakayasu and T. Yamaguchi, "Regioselective Direct Carboxylation of 2-Naphthol with Supercritical CO2 in the Presence of K2CO3," International Journal of Organic Chemistry, Vol. 3 No. 3, 2013, pp. 210-213. doi: 10.4236/ijoc.2013.33028.

References

[1] S. A. Lindsey and H. Jesky, “The Kolbe-Schmitt Reaction,” Chemical Reviews, Vol. 57, No. 4, 1957, pp. 583-620. doi:10.1021/cr50016a001
[2] F. Seidel, L. Wolf and H. Krause, “über die Bildungsweise der 2-Oxynaphthoesaure-(3),” Journal für Praktische Chemie, Vol. 91, No. 1-2, 1955, pp. 53-83. doi:10.1002/prac.19550020105
[3] W. H. Meek and C. H. Fuchsmann, “Carboxylation of Substituted Phenols in N,N-Dimethylamide Solvents at Atmospheric Pressure,” Journal of Chemical & Engineering Data, Vol. 14, No. 4, 1968, pp. 388-391. doi:10.1021/je60042a005
[4] T. Yamaguchi, N. Nagaoka and K. Takahashi, “The Carboxylation of Naphthols by Kolbe-Schmitt Reaction in the Homogeneous Solution,” The Chemical Society of Japan, No. 7, 1989, pp. 1164-1165.
[5] T. Iijima, T. Iwase and T. Yamaguchi, “Carboxylation of 2-Naphthol with Carbon Dioxide in Anisole,” Journal of the Japan Petroleum Institute, Vol. 49, No. 4, 2006, pp. 206-209. doi:10.1627/jpi.49.206
[6] T. Iijima, D. Takagi and T. Yamaguchi, “Carboxylation of 2-Naphthol in Kerosene,” Journal of the Japan Petroleum Institute, Vol. 31, No. 1, 2008, pp. 65-69. doi:10.1627/jpi.51.65
[7] J. Baxter and T. Yamaguhi, “Effect of Cation Capture by Crown Ether and Polar Solvent in the Carboxylation with CO2 of Alkali Metal 2-Naphtholate under Ordinary Conditions,” Journal of Chemical Research (S), 1997, pp. 374-375. doi:10.1039/A703432F
[8] T. Iijima and T. Yamaguchi, “The Improved Kolbe— Schmitt Reaction Using Supercritical Carbon Dioxide,” Tetahedron Letters, Vol. 48, No. 30, 2007, pp. 5309-5311. doi:10.1016/j.tetlet.2007.05.132
[9] T. Iijima and T. Yamaguchi, “Efficient Regioselective Carboxylation of Phenol to Salicylic Acid with Supercritical CO2 in the Presence of Aluminum Bromide,” Journal of Molecular Catalysis A: Chemical, Vol. 295, 2008, pp. 52-56. doi:10.1016/j.molcata.2008.07.017
[10] T. Iijima and T. Yamaguchi, “K2CO3-Catalyzed Direct Synthesis of Salicylic Acid from Phenol and Supercritical CO2,” Applied Catalysis A: General, Vol. 345, No. 1, 2008, pp. 12-17. doi:10.1016/j.apcata.2008.03.037
[11] S. Fujita, B. M. Bhanage, Y. Ikushima and M. Arai, “Synthesis of Dimethyl Carbonate from Carbon Dioxide and Methanol in the Presence of Methyl Iodide and Base Catalysts under Mild Conditions: Effect of Reaction Conditions and Reaction Mechanism,” Green Chemistry, Vol. 3, No. 2, 2001, pp. 87-91. doi:10.1039/b100363l
[12] T. Sakakura, Y. Saito, M. Okano, J. Choi and C. T. Sako, “Selective Conversion of Carbon Dioxide to Dimethyl Carbonate by Molecular Catalysis,” The Journal of Organic Chemistry, Vol. 63, No. 20, 1998, pp. 7095-7096. doi:10.1021/jo980460z
[13] J. F. Brennkeand and J. E. Chateauneuf, “Homogeneous Organic Reactions as Mechanistic Probes in Supercritical Fluids,” Chemical Reviews, Vol. 99, No. 2, 1999, pp. 433-452. doi:10.1021/cr970035q
[14] Y. Du, F.Cai, D.-L.Kong and L.-N. He, “Organic Solvent-Free Process for the Synthesis of Propylene Carbonate from Supercritical Carbon Dioxide and Propylene Oxide Catalyzed by Insoluble Ion Exchange Resins,” Green Chemistry, Vol. 7, No. 7, 2005, pp. 518-523. doi:10.1039/b500074b
[15] G. Steinebrunner, A. J. Dyson, B. Kirchner and H. Hanspeter, “Structural and Thermodynamic Properties of Fluid Carbon Dioxide from a New ab initio Potential Energy Surface,” Journal of Chemical Physics, Vol. 109, 1998, Article ID. 3153. doi:10.1063/1.476922
[16] K. Rah and B. Eu, “Density Fluctuations and Shear Viscosity of Molecular Liquids: Carbon Dioxide and Nitrogen,” Journal of Chemical Physics, Vol. 112, No. 16, 2000, pp. 7118-7138. doi: 0.1063/1.481306
[17] Z. Markovic, J. P. Engelbrecht and S. Markovic and Z. Naturforch, “Theoretical Study of the Kolbe-Schmitt Reaction Mechanism,” Zeitschrift für Naturforchung, Vol. 57a, 2002, pp. 812-818.
[18] Y. Kosugi, Y. Imaoka, F. Gotoh, M. A. Rahim, Y. Matsui and K. Sakanishi, “Carboxylations of Alkali Metal Phenoxides with Carbon Dioxide,” Organic & Biomolecular Chemistry, Vol. 1, No. 5, 2003, pp. 817-821. doi:10.1039/b210793g

  
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