Skip to main content
SpringerLink
Log in

New methods to synthesize phthalaldehyde and its diacetals

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new synthesis of phthalaldehyde that avoided formation of HBr involved treatment of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1: 6, 90 °C, 10 mol.% ZnCl2) to obtain acyclic diacetal without admixture of cyclic one (1,3-dimethoxy-1,3-dihydrobenzo-[c]furan) followed by hydrolysis to give the target dialdehyde. Phthalaldehyde reacted with CH(OMe)3 in the presence of trifluoroacetic acid to yield exclusively cyclic diacetal. Acyclic diacetal was phosphorylated by treatment with secondary chlorophosphines and by the reaction with PCl3 followed by treatment with PIII acid ester.

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

Similar content being viewed by others

References

  1. J. M. Snell, A. Weissberger, Org. Synth., 1940, Vol. 20, 92.

    Article  CAS  Google Scholar 

  2. F. Weygand, K. Vogelbach, K. Zimmermann, Chem. Ber., 1947, 80, 391; DOI: https://doi.org/10.1002/cber.19470800504.

    Article  CAS  Google Scholar 

  3. P. Ruggli, F. Brandt, Helv. Chim. Acta, 1944, 27, 274; DOI: https://doi.org/10.1002/hlca.19440270132.

    Article  CAS  Google Scholar 

  4. P. Ruggli, M. Mathez, Helv. Chim. Acta, 1946, 29, 1235; DOI: https://doi.org/10.1002/hlca.19460290536.

    Article  CAS  Google Scholar 

  5. P. C. Zhu, C. G. Roberts, Y. T. Murrieta, Pat. US 2005/171201, 2004.

  6. S. Wawzonek, R. E. Karll, J. Am. Chem. Soc., 1948, 70, 1666; DOI: https://doi.org/10.1021/Ja01184a517.

    Article  CAS  Google Scholar 

  7. G. Karlheinz, P. Klaus, H. Rudolf, Pat. US 2006/293542, 2005.

  8. K. Giselbrecht, W. Hillisch, Pat. US 2006/199870, 2005.

  9. B. N. Brewer, K. T. Mead, C. U. Pittman, K. Lu, P. C. Zhu, J. Heterocycl. Chem., 2006, 43, 361; DOI: https://doi.org/10.1002/Jhet.5570430216.

    Article  CAS  Google Scholar 

  10. P. C. Zhu, B. N. Brewer, K. Lu, Pat. US 2007/4808, 2006.

  11. B. Kayan, R. Oezen, A. M. Gizir, N. S. Kus, Org. Prep. Proced. Int., 2005, 37, 83; DOI: https://doi.org/10.1080/00304940509355405.

    Article  CAS  Google Scholar 

  12. K. Ohkubo, K. Suga, K. Morikawa, S. Fukuzumi, J. Am. Chem. Soc., 2003, 125, 12850; DOI: https://doi.org/10.1021/Ja036645r.

    Article  CAS  Google Scholar 

  13. A. G. Shoair, J. Mol. Liq., 2015, 206, 68; DOI: https://doi.org/10.1016/J.molliq.2015.01.023.

    Article  CAS  Google Scholar 

  14. A. Khorshidi, Chin. J. Catal., 2016, 37, 153; DOI: https://doi.org/10.1016/S1872-2067(15)61001-4.

    Article  CAS  Google Scholar 

  15. K. Tabatabaeian, M. A. Zanjanchi, N. O. Mahmoodi, T. Eftekhari, RSC Adv., 2015, 5, 101013; DOI: https://doi.org/10.1039/C5RA18179H.

    Article  CAS  Google Scholar 

  16. R. W. E. Reintjens, Q. B. Broxterman, M. Kotthaus, P. Poechlauer, Pat. WO 2007/134847.

  17. K. Endo, H. Takahashi, M. Aihara, Heterocycles, 1996, 42, 589; DOI: https://doi.org/10.3987/COM-95-S48.

    Article  CAS  Google Scholar 

  18. V. V. Namboodiri, V. Polshettiwar, R. S. Varma, Tetrahedron Lett., 2007, 48, 8839; DOI: https://doi.org/10.1016/J.tetlet.2007.10.068.

    Article  CAS  Google Scholar 

  19. E. Takezawa, S. Sakaguchi, Y. Ishii, Org. Lett., 1999, 1, 713; DOI: https://doi.org/10.1021/ol990117w.

    Article  CAS  Google Scholar 

  20. H. Firouzabadi, B. Vessal, M. Naderi, Tetrahedron Lett., 1982, 23, 1847; DOI: https://doi.org/10.1016/S0040-4039(00)86758-1.

    Article  CAS  Google Scholar 

  21. S. Li, L. Zhou, Z. Song, F. Bao, K. Kanno, T. Takahashi, Heterocycles, 2007, 73, 519; DOI: https://doi.org/10.3987/COM-07-S(U)28.

    Article  CAS  Google Scholar 

  22. K. Ariyoshi, Y. Aso, T. Otsubo, F. Ogura, Chem. Lett., 1984, 13, 891; DOI: https://doi.org/10.1246/cl.1984.891.

    Article  Google Scholar 

  23. N. G. Khaligh, Chin. J. Catal., 2014, 35, 329; DOI: https://doi.org/10.1016/S1872-2067(12)60750-5.

    Article  CAS  Google Scholar 

  24. N. G. Khaligh, F. Shirini, Ultrason. Sonochem., 2013, 20, 19; DOI: https://doi.org/10.1016/J.ultsonch.2012.07.016.

    Article  CAS  Google Scholar 

  25. F. Shirini, O. G. Jolodar, J. Mol. Catal. A: Chem., 2012, 356, 61; DOI: https://doi.org/10.1016/J.molcata.2012.01.002.

    Article  CAS  Google Scholar 

  26. J. S. Cha, S. W. Chang, J. Mi Kim, O. O. Kwon, J. C. Lee, Org. Prep. Proced. Int., 1997, 29, 665; DOI: https://doi.org/10.1080/00304949709355246.

    Article  CAS  Google Scholar 

  27. F. Weygand, G. Eberhardt, H. Linden, F. Schäfer, I. Eigen, Angew. Chem., 1953, 65, 525; DOI: https://doi.org/10.1002/ange.19530652102.

    Article  CAS  Google Scholar 

  28. R. J. P. Corriu, G. F. Lanneau, M. Perrot, Tetrahedron Lett., 1988, 29, 1271; DOI: https://doi.org/10.1016/S0040-4039(00)80274-9.

    Article  CAS  Google Scholar 

  29. F. Weygand, D. Tietjen, Chem. Ber., 1951, 84, 625; DOI: https://doi.org/10.1002/cber.19510840712.

    Article  CAS  Google Scholar 

  30. J. S. Cha, M. K. Jeoung, J. M. Kim, O. O. Kwon, J. C. Lee, Org. Prep. Proced. Int., 1994, 26, 583; DOI: https://doi.org/10.1080/00304949409458063.

    Article  CAS  Google Scholar 

  31. M. B. Smith, J. March, Marchś Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley and Sons, New York, 2013, 2047 pp.

    Google Scholar 

  32. L. A. Yanovskaya, S. S. Yufit, V. F. Kucherov, Khimiya atsetalei [Chemistry of Acetals], Nauka, Moscow, 1975, 273 pp. (in Russian).

    Google Scholar 

  33. E. Monroe, C. Hand, J. Am. Chem. Soc., 1950, 72, 5345; DOI: https://doi.org/10.1021/Ja01167a605.

    Article  CAS  Google Scholar 

  34. R. B. Moffett, Org. Synth., 1963, Coll. Vol. 4, 427.

    Google Scholar 

  35. K. Schank, Chem. Ber., 1967, 100, 2292; DOI: https://doi.org/10.1002/cber.19671000725.

    Article  CAS  Google Scholar 

  36. G. Cavallini, J. Med. Chem., 1964, 7, 255; DOI: https://doi.org/10.1021/Jm00333a003.

    Article  CAS  Google Scholar 

  37. E. Kober, C. Grundmann, J. Am. Chem. Soc., 1958, 80, 5547; DOI: https://doi.org/10.1021/Ja01553a058.

    Article  CAS  Google Scholar 

  38. A. Clerici, N. Pastori, O. Porta, Tetrahedron, 1998, 54, 15679; DOI: https://doi.org/10.1016/S0040-4020(98)00982-X.

    Article  CAS  Google Scholar 

  39. N. Hamada, K. Kazahaya, H. Shimizu, T. Sato, Synlett, 2004, 1074; DOI: https://doi.org/10.1055/s-2004-820038.

  40. M. B. Gazizov, K. M. Gazizov, M. A. Pudovik, A. A. Mukhamadiev, R. F. Karimova, A. I. Sadykova, O. G. Sinyashin, Dokl. Chem., 2001, 381, 321; DOI: https://doi.org/10.1023/A:1012928708045.

    Article  Google Scholar 

  41. M. B. Gazizov, S. Yu. Ivanova, N. Yu. Bashkirtseva, O. D. Khairullina, R. A. Khairullin, O. V. Gazizova, Russ. Chem. Bull., 2017, 66, 1230; DOI: https://doi.org/10.1007/s11172-017-1877-6.

    Article  CAS  Google Scholar 

  42. M. B. Gazizov, S. Yu. Ivanova, Sh. N. Ibragimov, K. S. Gazizova, R. A. Khairullin, K. A. Medvedeva, Russ. J. Gen. Chem., 2016, 86, 2132; DOI: https://doi.org/10.1134/S1070363216090279.

    Article  CAS  Google Scholar 

  43. M. R. Powell, D. R. Rexford, J. Org. Chem., 1953, 18, 810; DOI: https://doi.org/10.1021/Jo50013a006.

    Article  CAS  Google Scholar 

  44. E. Schmitz, Chem. Ber., 1958, 91, 410; DOI: https://doi.org/10.1002/cber.19580910228.

    Article  CAS  Google Scholar 

  45. R. S. McDonald, E. V. Martin, Can. J. Chem., 1979, 57, 506; DOI: https://doi.org/10.1139/v79-084.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Kazan National Research Technological University, 68 ul. K. Marx, 420015, Kazan, Russian Federation

    M. B. Gazizov, R. A. Khairullin, S. Yu. Ivanova, Yu. S. Kirillina, I. O. Romanenko & N. N. Gazizova

Authors
  1. M. B. Gazizov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. A. Khairullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Yu. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. S. Kirillina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. O. Romanenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. N. Gazizova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. B. Gazizov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1878–1882, October, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gazizov, M.B., Khairullin, R.A., Ivanova, S.Y. et al. New methods to synthesize phthalaldehyde and its diacetals. Russ Chem Bull 68, 1878–1882 (2019). https://doi.org/10.1007/s11172-019-2640-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2640-y

Key words

Search

Navigation