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Synthesis of Phthalic Aldehyde and Its Diacetals

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Abstract

Acyclic phthalaldehyde diacetal without cyclic 1,3-dihydro-1,3-dimethoxybenzo[c]furan impurity has been obtained via the reaction of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1:6) at 90°C in the presence of 10 mol% of ZnCl2. Hydrolysis of phthalaldehyde diacetal has led to the formation of phthalaldehyde without HBr evolution. The reaction of phthalaldehyde with trimethyl orthoformate in the presence of trifluoroacetic acid has proceeded abnormally, with the formation of the cyclic diacetal. The acyclic diacetal has been phosphorylated by chlorophosphines and the action of PCl3 and a P(III) acid ester in sequence.

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Funding

This study was financially supported by the Ministry of Education and Science of Russian Federation in the scope of the basic part of the State Task (project no. 4.5348.2017/8.9).

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Authors and Affiliations

  1. Kazan National Research Technological University, Kazan, 420015, Russia

    R. A. Khairullin, M. B. Gazizov, Yu. S. Kirillina, S. Yu. Ivanova, O. D. Khairullina & K. S. Gazizova

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  1. R. A. Khairullin
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  2. M. B. Gazizov
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  3. Yu. S. Kirillina
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  4. S. Yu. Ivanova
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Correspondence to M. B. Gazizov.

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No conflict of interest was declared by the authors.

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 11, pp. 1651–1658.

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Khairullin, R.A., Gazizov, M.B., Kirillina, Y.S. et al. Synthesis of Phthalic Aldehyde and Its Diacetals. Russ J Gen Chem 89, 2178–2184 (2019). https://doi.org/10.1134/S1070363219110021

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  • DOI: https://doi.org/10.1134/S1070363219110021

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