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Regioselective Direct Carboxylation of 2-Naphthol with Supercritical CO<sub>2</sub> in the Presence of K<sub>2</sub>CO<sub>3</sub>
College of Industrial Technology, Nihon University, Chiba, Japan
College of Industrial Technology, Nihon University, Chiba, Japan
Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan
Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan Instrumental Analysis Division, Center for Supports to Research and Education Activities, Kobe University, Kobe, Japan
Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan
- 1 College of Industrial Technology, Nihon University, Chiba, Japan
- 2 College of Industrial Technology, Nihon University, Chiba, Japan
- 3 Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan
- 4 Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan Instrumental Analysis Division, Center for Supports to Research and Education Activities, Kobe University, Kobe, Japan
- 5 Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan
International Journal of Organic Chemistry·Volume 03 (2013)·Pages 210–213·Published 27 August 2013·DOI10.4236/ijoc.2013.33028
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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 K 2 CO 3 (10-fold molar to 2-naphthol) under supercritical CO 2 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 K 2 CO 3 . Theoretical explanation about the regioselectivity was achieved by means of DFT calculations.
KeywordsSupercritical CO<sub>2</sub>CO<sub>2</sub>UtilizationKolbe-Schmitt ReactionCarboxylation2-NaphtholPotassium Carbonate2-Hydroxynaphthalene-6-carboxylic AcidDFT Calculation
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