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