Kim, DW Hong, DJ Seo, JW Kim, HS Kim, HK Song, CE Chi, DY 2024-01-21T07:09:52Z 2024-01-21T07:09:52Z 2021-09-01 2004-04-30 0022-3263 https://pubs.kist.re.kr/handle/201004/137662 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. English AMER CHEMICAL SOC Hydroxylation of alkyl halides with water in ionic liquid: Significantly enhanced nucleophilicity of water Article 10.1021/jo035563i 1 JOURNAL OF ORGANIC CHEMISTRY, v.69, no.9, pp.3186 - 3189 JOURNAL OF ORGANIC CHEMISTRY 69 9 3186 3189 scie scopus 000221268200036 2-s2.0-2142643682 Chemistry, Organic Chemistry Article hydroxylation alkyl halides ionic liquid nucleophilicity