An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols

A. I. Zinin, E. V. Stepanova, U. Jost, N. N. Kondakov, A. M. Shpirt, A. O. Chizhov, V. I. Torgov, L. O. Kononov

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Efficient multigram two-step syntheses of 4-(2-chloroethoxy)phenol and 4-(3-chloropropoxy)phenol in >70% yields starting from 4-hydroxybenzaldehyde and reagents with general formula Cl(CH2)nX (X = Cl, n = 2; X = OTs, n = 3) are proposed. 4-(2-Chloroethoxy)phenol can also be conveniently prepared from 4-methoxyphenol and 1,2-dichloroethane. The compounds thus obtained can be used in carbohydrate chemistry to synthesize glycosides bearing "universal" 4-(ω-chloroalkoxy)phenyl aglycons.

Original languageEnglish
Pages (from-to)304-312
Number of pages9
JournalRussian Chemical Bulletin
Volume66
Issue number2
DOIs
Publication statusPublished - 1 Feb 2017

Keywords

  • 4-(ω-chloroalkoxy)phenols
  • anomeric protective groups
  • heterobifunctional building blocks
  • phenols
  • selective demethylation

ASJC Scopus subject areas

  • Chemistry(all)

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  • Cite this

    Zinin, A. I., Stepanova, E. V., Jost, U., Kondakov, N. N., Shpirt, A. M., Chizhov, A. O., Torgov, V. I., & Kononov, L. O. (2017). An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols. Russian Chemical Bulletin, 66(2), 304-312. https://doi.org/10.1007/s11172-017-1732-9