2-(Chloromethyl)-3,5-dioxahex-1-ene. An Effective Acetonylating Reagent

Article abstract of DOI:10.1021/jo00391a003

By β-elimination of 2-chloro-1-(chloromethyl)ethyl methoxymethyl ether (1) under solid-liquid phase-transfer catalytic conditions, 2-(chloromethyl)-3,5-dioxahex-1-ene (2) of high purity was readily obtained in 85percent.Allyl chloride (2) is found to be stable at ambient conditions and to be a superior reagent as CH3COCH2⁺ synthon for converting active proton-containing compounds such as carboxylic acids, amines, phenols, alcohols, thiols, malonate, β-diketones, β-keto esters, phenylacetonitrile, fluorene, and indene to the corresponding acetonyl derivatives in good to excellent yields (61-93percent), usually under phase-transfer catalytic conditions or in a t-BuONa-t-BuOH system.