title: Hydroxylation of alkyl halides with water in ionic liquid: significantly enhanced nucleophilicity of water.
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.
authors.affiliation: Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea.
authors.forename: Dong Wook
authors.initials: DW
authors.lastname: Kim
authors.forename: Dong Jin
authors.initials: DJ
authors.lastname: Hong
authors.forename: Jai Woong
authors.initials: JW
authors.lastname: Seo
authors.forename: Hoon Sik
authors.initials: HS
authors.lastname: Kim
authors.forename: Hong Kon
authors.initials: HK
authors.lastname: Kim
authors.forename: Choong Eui
authors.initials: CE
authors.lastname: Song
authors.forename: Dae Yoon
authors.initials: DY
authors.lastname: Chi