Skip to main content
SpringerLink
Log in

New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A new approach has been developed for the synthesis of o-ketobenzoic pseudo-acid chlorides via dehalogenation of bromo-substituted cyclic o-ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid chloride con­taining a biphenyl fragment, which could not be obtained by the traditional method involving acylation of biphenyl and subsequent chlorination of the diacid thus formed owing to deactivation of the second para-position in the aromatic fragment. The proposed approach solves the problem of poor solubility of poly­phenylene diacids with more than three phenylene rings and makes it possible to synthesize a bis-pseudo-acid chloride with a quaterphenyl fragment.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Bhatt, M.V. and Kamath, K.M., J. Chem. Soc. B, 1968, p. 1036. https://doi.org/10.1039/J29680001036

  2. Bhatt, M.V., Kamath, K.M., and Ravindranathan, M., J. Chem. Soc. C, 1971, p. 1772. https://doi.org/10.1039/J39710001772

  3. Salazkin, S.N., Korshak, V.V., Vinogradova, S.V., Melekhina, G.N., Kul’kov, A.A., and Komarova, L.I., Polym. Sci. U.S.S.R., 1977, vol. 19, p. 212. https://doi.org/10.1016/0032-3950(77)90169-1

    Article  Google Scholar 

  4. Salazkin, S.N., Polym. Sci., Ser. B, 2004, vol. 46, p. 203.

    Google Scholar 

  5. Zolotukhin, M.G., Egorov, E.A., Sedova, E.A., Soroki­na, Y.L., Kovardakov, V.A., Salazkin, S.N., and Sangalov, Y.A., Dokl. Chem., 1990, vol. 311, p. 123.

    Google Scholar 

  6. Salazkin, S.N., Rafikov, S.R., Tolstikov, G.A., and Zolotukhin, M.G., Dokl. Chem., 1982, vol. 262, p. 355.

    CAS  Google Scholar 

  7. Salazkin, S.N., Shaposhnikova, V.V., Machulenko, L.M., Gileva, N.G., Kraikin, V.A., and Lachinov, A.N., Polym. Sci., Ser. A, 2008, vol. 50, p. 243. https://doi.org/10.1007/s11498-008-3002-y

    Article  Google Scholar 

  8. Yusupov, A.R., Rakhmeev, R.G., Lachinov, A.N., Kali­mullina, L.R., Nakaryakov, A.S., and Bunakov, A.A., Phys. Solid State, 2013, vol. 55, p. 1494. https://doi.org/10.1134/S1063783413070342

    Article  CAS  Google Scholar 

  9. Lezhnev, S.K., Yusupov, A.R., Galiev, A.F., Korni­lov, V.M., Gadiev, R.M., and Lachinov, A.N., JETP Lett., 2019, vol. 110, p. 447. https://doi.org/10.1134/S0021364019190093

    Article  CAS  Google Scholar 

  10. Lachinov, A.A., Karamov, D.D., and Lachinov, A.N., Semiconductors, 2021, vol. 55, p. 202. https://doi.org/10.1134/S1063782621020184

    Article  CAS  Google Scholar 

  11. Zil’berg, R.A., Yarkaeva, Yu.A., Maksyutova, E.I., Sidel’nikov, A.V., and Maistrenko, V.N., J. Anal. Chem., 2017, vol. 72, p. 402. https://doi.org/10.1134/S1061934817040177

    Article  Google Scholar 

  12. Zil’berg, R.A., Maistrenko, V.N., Yarkaeva, Yu.A., and Dubrovskii, D.I., J. Anal. Chem., 2019, vol. 74, p. 1245. https://doi.org/10.1134/S1061934819110133

    Article  Google Scholar 

  13. Yarkaeva, Y.A., Dubrovskii, D.I., Zil’berg, R.A., and Maistrenko, V.N., Russ. J. Electrochem., 2020, vol. 56, p. 544. https://doi.org/10.1134/S102319352007006X

    Article  CAS  Google Scholar 

  14. Wolfe, J.F. and Stille, J.K., Macromolecules, 1976, vol. 9, p. 489. https://doi.org/10.1021/ma60051a020

    Article  CAS  Google Scholar 

  15. Colon, I. and Kelsey, D.R., J. Org. Chem., 1986, vol. 51, p. 2627. https://doi.org/10.1021/jo00364a002

    Article  CAS  Google Scholar 

  16. Yangirov, T.A., Fatykhov, A.A., Sedova, E.A., Gileva, N.G., Khafizova, R.R., Meshcheryakova, E.S., Khalilov, L.M., and Kraikin, V.A., Russ. J. Org. Chem., 2019, vol. 55, p. 670. https://doi.org/10.1134/S1070428019050142

    Article  CAS  Google Scholar 

  17. Newman, M.S. and Lala, L.K., Tetrahedron Lett., 1967, vol. 8, no. 34, p. 3267. https://doi.org/10.1016/S0040-4039(01)89866-X

    Article  Google Scholar 

  18. Kovardakov, V.A., Cand. Sci. (Chem.) Dissertation, Ufa, 1983.

  19. Bhatt, M.V., Kamath, K.M., and Ravindranathan, M., J. Chem. Soc. C, 1971, p. 3344. https://doi.org/10.1039/J39710003344

  20. Groggins, P.H., Ind. Eng. Chem., 1930, vol. 22, p. 620. https://doi.org/10.1021/ie50246a019

    Article  CAS  Google Scholar 

  21. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  22. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The spectral data and elemental analyses were obtained using the equipment of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences). X-Ray analysis was performed at the Agidel joint center (Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment “Synthesis and Properties of (Co)polyarylene­phthalides with Different Types of Attachment of Phthalide Groups (head-to-head and head-to-tail)” (project no. 122031400279-9).

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    T. A. Yangirov, N. G. Gileva, A. A. Fatykhov & V. A. Kraikin

  2. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

    E. S. Meshcheryakova & L. M. Khalilov

Authors
  1. T. A. Yangirov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. G. Gileva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Fatykhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. S. Meshcheryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Kraikin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Kraikin.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 9, pp. 1000–1006 https://doi.org/10.31857/S0514749222090099.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yangirov, T.A., Gileva, N.G., Fatykhov, A.A. et al. New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides. Russ J Org Chem 58, 1254–1259 (2022). https://doi.org/10.1134/S1070428022090093

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022090093

Keywords:

Search

Navigation