Skip to main content
Log in

Selective functionalization of the primary hydroxy group in triols

  • Various Physicochemical and Technological Processes
  • Published:
Russian Journal of Applied Chemistry Aims and scope Submit manuscript

Abstract

A procedure was suggested for preparing functionally substituted 1,2-diols by O-alkylation of hydroxyalkyl-1,3-dioxacyclanes with alkyl halides, followed by acid hydrolysis. The conditions for selective cleavage of the ethers obtained were found. (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate under the conditions of acid deacetalization undergoes saponification of the ester group.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Green, T.W. and Wuts, P.G.M., New York: Wiley–Interscience, 1999, pp. 308–322, 724–727.

    Google Scholar 

  2. Sartori, G., Ballini, R., Bigi, F., et al., Chem. Rev., 2004, vol. 104, pp. 199–250.

    Article  CAS  Google Scholar 

  3. Bogomazova, A.A., Mikhailova, N.N., and Zlotskii, S.S., Modern Chemistry of Cyclic Acetals. Preparation, Reactions, Properties, Saarbrücken: Lambert Academic, 2012.

    Google Scholar 

  4. Yong Xu, Lian Qian, Pontsler, A.V., et al., Tetrahedron, 2004, vol. 60, pp. 43–49.

    Article  CAS  Google Scholar 

  5. Clinch, K., Evans, G.B., Frohlich, R.F.G., et al., J. Med. Chem., 2009, vol. 52, pp. 1126–1143.

    Article  CAS  Google Scholar 

  6. Valiev, V.F., Raskil’dina, G.Z., Mudrik, T.P., et al., Bashk. Khim. Zh., 2014, vol. 21, no. 3, pp. 25–27.

    CAS  Google Scholar 

  7. Merino, P., Franco, S., Mates, J.A., et al., ARKIVOC, 2004, vol. 4, pp. 48–58.

    Google Scholar 

  8. Shepherd, J.N. and Myles, D.C., Org. Lett., 2003, vol. 5, no. 7, pp. 586–593.

    Article  Google Scholar 

  9. Ariza, X., Costa, A.M., Faja, M., et al., Org. Lett., 2000, vol. 2, no. 18, pp. 2809–2811.

    Article  CAS  Google Scholar 

  10. Raskil’dina, G.Z., Valiev, V.F., Sultanova, R.M., and Zlotskii, S.S., Izv. Ross. Akad. Nauk, Ser. Khim., 2015, no. 9, pp. 2095–2099.

    Google Scholar 

  11. Kazemi, F., Kiasat, A.R., and Ebrahimi, S., Synth. Commun., 2005, vol. 35, pp. 1441–1445.

    Article  CAS  Google Scholar 

  12. Cichy, A.F., Saibaba, R., El Subbagh, H.I., et al., J. Org. Chem., 1991, vol. 56, pp. 4653–4658.

    Article  CAS  Google Scholar 

  13. Xu, J., Yang, D., Li, W., et al., Polymer, 2011, vol. 52, pp. 4268–4276.

    Article  CAS  Google Scholar 

  14. Chen, C.-T. and Munot, Y.S., J. Org. Chem., 2005, vol. 70, pp. 8625–8627.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. Z. Raskil’dina.

Additional information

Original Russian Text © G.Z. Raskil’dina, V.F. Valiev, R.M. Sultanova, S.S. Zlotskii, 2015, published in Zhurnal Prikladnoi Khimii, 2015, Vol. 88, No. 10, pp. 1414-1419.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Raskil’dina, G.Z., Valiev, V.F., Sultanova, R.M. et al. Selective functionalization of the primary hydroxy group in triols. Russ J Appl Chem 88, 1599–1604 (2015). https://doi.org/10.1134/S1070427215100079

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070427215100079

Keywords

Navigation