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One-pot synthesis of cyclic aldol tetramer and α, β-unsaturated aldol from linear aldehydes using quaternary ammonium combined with sodium hydroxide as catalysts

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Abstract

One-pot synthesis of cyclic aldol tetramer and α, β-unsaturated aldol from C3-C8 linear aldehydes using phase-transfer catalyst (PTC), quaternary ammonium, combined with sodium hydroxide as catalysts was investigated. Butanal was subjected for detail investigations to study the effect of parameters. It was found that the selectivity of cyclic aldol tetramer depends greatly on the operating conditions of the reaction, especially the PTC/butanal molar ratio. The average selectivity of 2-hydroxy-6-propyl-l, 3, 5-triethyl-3-cyclohexene-1-carboxaldehyde (HPTECHCA) was 54.41% using tetrabutylammonium chloride combined with 14% (mass fraction) NaOH as catalysts at 60 °C for 2 h with a PTC-to-butanal molar ratio of 0.09:1. Pentanal was more likely to generate cyclic aldol tetramer compared with other aldehydes under the optimum experimental conditions. Recovery of the PTC through water washing followed by adding enough sodium hydroxide from the washings was also demonstrated.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China

    Hai-feng Xu  (许海峰), Hong Zhong  (钟宏), Shuai Wang  (王帅) & Fang-xu Li  (李方旭)

  2. Key Laboratory of Resources Chemistry of Nonferrous Metals of Ministry of Education, Central South University, Changsha, 410083, China

    Hai-feng Xu  (许海峰), Hong Zhong  (钟宏), Shuai Wang  (王帅) & Fang-xu Li  (李方旭)

Authors
  1. Hai-feng Xu  (许海峰)
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  2. Hong Zhong  (钟宏)
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  3. Shuai Wang  (王帅)
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  4. Fang-xu Li  (李方旭)
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Corresponding author

Correspondence to Hong Zhong  (钟宏).

Additional information

Foundation item: Project(2013AA064102) supported by the National High-Tech Research Program of China; Project(11JJ6014) supported by the Hunan Provincial Natural Science Foundation of China

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Xu, Hf., Zhong, H., Wang, S. et al. One-pot synthesis of cyclic aldol tetramer and α, β-unsaturated aldol from linear aldehydes using quaternary ammonium combined with sodium hydroxide as catalysts. J. Cent. South Univ. 22, 2081–2087 (2015). https://doi.org/10.1007/s11771-015-2732-2

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  • DOI: https://doi.org/10.1007/s11771-015-2732-2

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