Skip to main content
SpringerLink
Log in

Optical resolution of racemic 4-hydroxy-3-isobornyl-5-methylbenzaldehyde

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

Abstract

Racemic 4-hydroxy-3-isobornyl-5-methylbenzaldehyde was separated into particular enantiomers via transformation into diastereoisomeric Schiff bases by reaction with (R)-1-phenylethanamine. The absolute configuration of the products was determined on the basis of the X-ray diffraction data for camphanate derived from one enantiomer of 4-hydroxy-3-isobornyl-5-methylbenzaldehyde.

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. Gerasimova, O.A., Milaeva, E.R., Shpakovskii, D.B., Semeikin, A.S., and Syrbu, S.A., Russ. Chem. Bull., 2007, vol. 56, p. 831.

    Article  CAS  Google Scholar 

  2. Unangst, P.C., Connor, D.T., Cetenko, W.A., Sorenson, R.J., Kostlan, C.R., Sircar, J.C., Wright, C.D., Schrier, D.J., and Dyer, R.D., J. Med. Chem., 1994, vol. 37, p. 322.

    Article  CAS  Google Scholar 

  3. Hori, H., Nagasawa, H., Ishibashi, M., Uto, Y., Hirata, A., Saijo, K., Ohkura, K., Kork, K.L., and Uehara, Y., Bioorg. Med. Chem., 2002, vol. 10, p. 3257.

    Article  CAS  Google Scholar 

  4. Boldron, C., Özalp-Yaman, Ş., Gamez, P., Tooke, D.M., Spek, A.L., and Reedijk, J., J. Chem. Soc., Dalton Trans., 2005, p. 3535.

  5. Prishchenko, A.A., Livantsov, M.V., Novikova, O.P., Livantsova, L.I., Shpakovskii, D.B., and Milaeva, E.R., Russ. J. Gen. Chem., 2006, vol. 76, p. 1753.

    Article  CAS  Google Scholar 

  6. Plotnikov, M.B., Smolyakova, V.I., Ivanov, I.S., Kuchin, A.V., Chukicheva, I.Yu., Buravlev, E.V., and Krasnov, E.A., Pharm. Chem. J., 2010, vol. 44, p. 530.

    Article  Google Scholar 

  7. Chukicheva, I.Yu., Buravlev, E.V., Fedorova, I.V., Borisenkov, M.F., and Kutchin, A.V., Russ. Chem. Bull., 2010, vol. 59, p. 2276.

    Article  CAS  Google Scholar 

  8. Buravlev, E.V., Chukicheva, I.Yu., Dolgushin, F.M., and Kuchin, A.V., Russ. J. Org. Chem., 2010, vol. 46, p. 649.

    Article  CAS  Google Scholar 

  9. Niyazov, N.A. and Pantukh, B.I., Russian Patent no. 2 063 399, 1996; Byull. Izobret., 1996, no. 19.

  10. Buravlev, E.V., Chukicheva, I.Yu., Suponitsky, K.Yu., Vikharev, Yu.B., Grishko, V.V., and Kutchin, A.V., Lett. Org. Chem., 2011, vol. 8, p. 301.

    Article  CAS  Google Scholar 

  11. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Komi Research Center, Ural Division, Russian Academy of Sciences, ul. Pervomaiskaya 48, Syktyvkar, 167982, Russia

    E. V. Buravlev, I. Yu. Chukicheva & A. V. Kutchin

  2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    A. V. Churakov

Authors
  1. E. V. Buravlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. Yu. Chukicheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Churakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Kutchin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Buravlev.

Additional information

Original Russian Text © E.V. Buravlev, I.Yu. Chukicheva, A.V. Churakov, A.V. Kutchin, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 1, pp. 70–74.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buravlev, E.V., Chukicheva, I.Y., Churakov, A.V. et al. Optical resolution of racemic 4-hydroxy-3-isobornyl-5-methylbenzaldehyde. Russ J Org Chem 48, 64–68 (2012). https://doi.org/10.1134/S1070428012010095

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428012010095

Keywords

Search

Navigation