Email this article An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols
- Authors: Zinin A.I.1, Stepanova E.V.1,2, Jost U.1,3, Kondakov N.N.1, Shpirt A.M.1, Chizhov A.O.1, Torgov V.I.1, Kononov L.O.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- National Research Tomsk Polytechnic University
- Institut für Chemie, Universität Rostock
- Issue: Vol 66, No 2 (2017)
- Pages: 304-312
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240016
- DOI: https://doi.org/10.1007/s11172-017-1732-9
- ID: 240016
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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)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.
About the authors
A. I. Zinin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
E. V. Stepanova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; National Research Tomsk Polytechnic University
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 30 prosp. Lenina, Tomsk, 634050
U. Jost
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Institut für Chemie, Universität Rostock
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991; Albert-Einstein-Str. 3A, Rostock, 18059
N. N. Kondakov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. M. Shpirt
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. O. Chizhov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
V. I. Torgov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
L. O. Kononov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: leonid.kononov@gmail.com
Russian Federation, 47 Leninsky prosp., Moscow, 119991
