Hydroxylation of Alkyl Halides with Water in Ionic Liquid

Significantly Enhanced Nucleophilicity of Water

Dong Wook Kim, Dong Jin Hong, Jai Seo, Hoon Sik Kim, Hong Kon Kim, Choong Eui Song, Dae Yoon Chi

Research output: Contribution to journalArticle

70 Citations (Scopus)

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] [BF 4]) 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.

Original languageEnglish (US)
Pages (from-to)3186-3189
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number9
DOIs
StatePublished - Apr 30 2004
Externally publishedYes

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Ionic Liquids
Hydroxylation
Water
Mesylates
Phenol
Acetic Acid
Alcohols
Oxygen
naphthalene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hydroxylation of Alkyl Halides with Water in Ionic Liquid : Significantly Enhanced Nucleophilicity of Water. / Kim, Dong Wook; Hong, Dong Jin; Seo, Jai; Kim, Hoon Sik; Kim, Hong Kon; Song, Choong Eui; Chi, Dae Yoon.

In: Journal of Organic Chemistry, Vol. 69, No. 9, 30.04.2004, p. 3186-3189.

Research output: Contribution to journalArticle

Kim, Dong Wook ; Hong, Dong Jin ; Seo, Jai ; Kim, Hoon Sik ; Kim, Hong Kon ; Song, Choong Eui ; Chi, Dae Yoon. / Hydroxylation of Alkyl Halides with Water in Ionic Liquid : Significantly Enhanced Nucleophilicity of Water. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 9. pp. 3186-3189.
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