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Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation
College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
School of Chemical and Environmental Engineering, Beijing Technology and Business University, Beijing 100048, China
* Author to whom correspondence should be addressed.
Received: 30 September 2010; in revised form: 20 October 2010 / Accepted: 21 October 2010 / Published: 25 October 2010
Abstract: Rapid synthesis of 4-ethyloctanoic acid by means of microwave irradiation is described. Diethyl malonate reacted with 2-ethyl-1-bromohexane in the presence of sodium ethoxide to give diethyl (2-ethylhexyl)malonate (1b). 1b was saponified in the solution of ethanol and potassium hydroxide and then acidified to form (2-ethylhexyl)propanedioic acid (1c), and 1c was heated and decarboxylized to give 4-ethyloctanoic acid (1d). The influence of reaction temperature and reaction time on the yield of 1b and the effect of reaction time on the yield of 1c and 1d were investigated in order to optimize the synthetic conditions. The relative optimal conditions for the synthesis of 1b were a mole ratio of sodium to diethyl malonate to 2-ethylhexyl bromide of 0.1:0.11:0.11, a reaction temperature of 80–85 °C, and a reaction time of 2–2.5 h. The yield of 1b was about 79%. 1b was saponified for 30 min and then acidified to form 1c, and the yield of 1c was 96%. 1c was heated for 16 min at 180°C to give 1d, and the yield of 1d was about 90%. The overall yield of 1d is 70% under microwave irradiation. The reaction time was reduced greatly. In order to compare the result of microwave irradiation with that of an oil bath, the reactions were also performed in an oil bath. The structures of intermediates, product and by-product were confirmed by HRMS, 1H NMR, 13C-NMR and IR.
Keywords: 4-ethyloctanoic acid; microwave irradiation; diethyl malonate; diethyl (2-ethylhexyl)malonate; (2-ethylhexyl)propanedioic acid
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Liu, Y.-P.; Yin, D.-C.; Chen, H.-T.; Sun, B.-G. Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation. Int. J. Mol. Sci. 2010, 11, 4165-4174.
Liu Y-P, Yin D-C, Chen H-T, Sun B-G. Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation. International Journal of Molecular Sciences. 2010; 11(10):4165-4174.
Liu, Yu-Ping; Yin, De-Cai; Chen, Hai-Tao; Sun, Bao-Guo. 2010. "Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation." Int. J. Mol. Sci. 11, no. 10: 4165-4174.