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 School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	304-312
Number of pages	9
Journal	Russian Chemical Bulletin
Volume	66
Issue number	2
DOIs	https://doi.org/10.1007/s11172-017-1732-9
Publication status	Published - 1 Feb 2017

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1007/s11172-017-1732-9

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title = "An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols",

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.",

keywords = "4-(ω-chloroalkoxy)phenols, anomeric protective groups, heterobifunctional building blocks, phenols, selective demethylation",

author = "Zinin, {A. I.} and Stepanova, {E. V.} and U. Jost and Kondakov, {N. N.} and Shpirt, {A. M.} and Chizhov, {A. O.} and Torgov, {V. I.} and Kononov, {L. O.}",

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doi = "10.1007/s11172-017-1732-9",

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journal = "Russian Chemical Bulletin",

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T1 - An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols

AU - Zinin, A. I.

AU - Stepanova, E. V.

AU - Jost, U.

AU - Kondakov, N. N.

AU - Shpirt, A. M.

AU - Chizhov, A. O.

AU - Torgov, V. I.

AU - Kononov, L. O.

PY - 2017/2/1

Y1 - 2017/2/1

N2 - 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.

AB - 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.

KW - 4-(ω-chloroalkoxy)phenols

KW - anomeric protective groups

KW - heterobifunctional building blocks

KW - phenols

KW - selective demethylation

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