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Hydroxylation of Alkyl Halides with Water in Ionic Liquid: Significantly Enhanced Nucleophilicity of Water

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Dong Wook Kim,^† Dong Jin Hong,^† Jai Woong Seo,^† Hoon Sik Kim,^‡ Hong Kon Kim,^‡ Choong Eui Song,^‡ and Dae Yoon Chi*^†

Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea, and Reaction Media Research Center and Life Sciences Division, Korea Institute of Science and Technology, Cheongryang, Seoul 130-650, Korea dychi@inha.ac.kr

J. Org. Chem., 2004, 69 (9), pp 3186–3189

DOI: 10.1021/jo035563i

Publication Date (Web): March 24, 2004

†

Inha University.

‡

Korea Institute of Science and Technology.

To whom correspondence should be addressed. Tel: +82-32-860-7686. Fax: +82-32-867-5604.

Abstract

A facile method for the nucleophilic hydroxylation of alkyl halides and mesylates with water has been developed in which the use of ionic liquid as an alternative reaction medium not only enhanced the nucleophilicity of water but also reduced the formation of elimination products predominantly formed under the conventional basic reaction conditions. For example, hydroxylation of model compound 2-(3-bromopropyl)naphthalene (1) to 2-(3-hydroxypropyl)naphthalene (2) with water in 1-n-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF₄]) and 1,4-dioxane proceeded selectively in high yield (94%). The reactivity of other nucleophilic oxygen sources such as alcohol, phenol, and acetic acid in an ionic liquid was also investigated.

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Published In Issue April 30, 2004
Received October 22, 2003

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Hydroxylation of Alkyl Halides with Water in Ionic Liquid: Significantly Enhanced Nucleophilicity of Water