Preview

Proceedings of the National Academy of Sciences of Belarus, Chemical Series

Advanced search

Аn improved method for preparation of heptyl (4-trifluoroacetyl) benzoate

https://doi.org/10.29235/1561-8331-2019-55-2-171-174

Abstract

A convenient three-step method for synthesis of heptyl (4-trifluoroacetyl)benzoate, an important neutral anion carrier, has been developed. The key step of the method is acylation of toluene by trifluoroacetic anhydride in presence of aluminium chloride at –8 – –10 oC. The procedure gives high overall yield and, unlike the earlier methods, does not include any organometallic reagents, therefore allowing scaling it up to several hundred grams, that makes the target compound much more readily available.

About the Authors

P. V. Senin
Atotech-Khemeta Ltd.
Russian Federation

Pavel V. Senin – Sales Engineer, Atotech-Khemeta Ltd.

73, Volokolamskoe Highway, offce 623, 125424, Moscow



L. S. Stanishevskii
Belarusian State University
Belarus
Leonid S. Stanishevskii – D. Sc. (Chemistry), Professor


Y. B. Akayeu
Belarusian State University
Belarus

Yauhen B. Akayeu – Ph. D. (Chemistry), Associate Professor, Leading Researcher

14, Leningradskaya Str., 220030, Minsk



References

1. Sessler J. L., Gale P. A., Cho W.-S. Anion Receptor Chemistry. Cambridge, Royal Society of Chemistry, 2006. 413 p.

2. Behringer C., Lehmann B., Haug J-P., Seiler K., Morf W. E., Hartman K., Simon W. Anion selectivities of trifluoroacetophenone derivatives as neutral ionophores in solvent-polymeric membranes. Analytica Chimica Acta., 1990, vol. 233, pp. 41–47. https://doi.org/10.1016/s0003-2670(00)83459-5

3. Knuniants I. L., Yakobson G. G. (eds.). Syntheses of organofluorine compounds: monomers and intermediate products. Moscow, Khimiya Publ., 1977, pp. 251–253 (in Russian).

4. Bourne E. J., Stacey M., Tatlow J. C., Tedder J. M. Studies of trifluoroacetic acid. Part III. The use of trifluoroacetic anhydride in the synthesis of aromatic ketones and sulphones. Journal of the Chemical Society (Resumed), 1951, pp. 718–720. https://doi.org/10.1039/jr9510000718

5. Ruiz J., Gilbert L., Astruc D. CoCl2 catalyzed trifluoroacetylation of aromatics using trifluoroacetic anhydride. Industrial Chemistry Library. Vol. 8. The Roots of Organic Development, 1996, pp. 39–47. https://doi.org/10.1016/s0926-9614(96)80008-6

6. Hojo M., Masuda R., Okada E. Nucleophilic nitrogen-nitrogen exchange reaction at aromatic carbon atoms – reaction of N,N-dimethyl-2,4-bistrifluoroacetyl-1-naphthylamine with various amines. Tetrahedron Letters, 1987, vol. 28, no 49, pp. 6199–6200. https://doi.org/10.1016/s0040-4039(00)61845-2

7. Anderson A. G., Anderson R. J. The Reaction of Azulenes with Trifluoro- and Trichloroacetic Anhydride. Journal of Organic Chemistry, 1962, vol. 27, no. 10, pp. 3578–3581. https://doi.org/10.1021/jo01057a044

8. Simchen G., Schmidt A. Eine einfache Methode zur Darstellung von Aryl-trifluormethylketonen. Synthesis, 1996, no. 9, pp. 1093–1094. https://doi.org/10.1055/s-1996-4444

9. Matveichuk Y., Akayeu Y., Rakhman’ko E. Hydration of p-trifluoroacetyl benzoic acid heptyl ester: how it affects analytical characteristics of sulfate selective electrodes based on higher quaternary ammonium salts. Chemical Papers, 2018, vol. 72, no. 2, pp. 509–514. https://doi.org/10.1007/s11696-017-0294-5


Review

Views: 921


Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.


ISSN 1561-8331 (Print)
ISSN 2524-2342 (Online)