Synthesis of Dodecyltrimethylammonium Bromochromate: An Improved Cr(VI)-Oxidant Reagent for Organic Substrates

Abstract

Orange-brown crystalline dodecyltrimethylammonium bromochromate, (C₁₂H₂₅)N(CH₃)₃[CrO₃Br], is easily prepared in a nearly quantitative yield by the interaction of dodecyltrimethylammonium bromide with CrO₃ molar ratio. This reagent is versatile for the effective and selective oxidation of organic substrates, in particular for alcohols, under mild conditions. The reagent in CH₂Cl₂ readily oxidizes primary and secondary alcohols to the corresponding carbonyls, carbohydrate to ketosugre, anthracene and phenanthrene to anthraquinone and phenanthraquinone, respectively.