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

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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) n X (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.

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Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

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

  2. National Research Tomsk Polytechnic University, 30 prosp. Lenina, 634050, Tomsk, Russian Federation

    E. V. Stepanova

  3. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3A, 18059, Rostock, Germany

    U. Jost

Authors
  1. A. I. Zinin
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  2. E. V. Stepanova
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  3. U. Jost
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  4. N. N. Kondakov
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  5. A. M. Shpirt
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  6. A. O. Chizhov
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  7. V. I. Torgov
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  8. L. O. Kononov
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Correspondence to L. O. Kononov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0304—0312, February, 2017.

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Zinin, A.I., Stepanova, E.V., Jost, U. et al. An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols. Russ Chem Bull 66, 304–312 (2017). https://doi.org/10.1007/s11172-017-1732-9

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  • DOI: https://doi.org/10.1007/s11172-017-1732-9

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