Methyl iodide → 6-Methoxy-2,4-bis(trichloromethyl)-2H,4H-1,3-benzodioxine

Participants

Reaction Steps

A solution of sodium hydroxide (0.52 g.) in ethanol (50 ml.) was added dropwise to a stirred solution of 6-hydroxy-2,4-bis(trichloromethyl)benzo[1,3]dioxin (5 g.) in ethanol (100 ml.) and the resulting solution was stirred for 15 minutes. Methyl iodide (1.7 ml.) was then added, the reaction mixture was warmed on a steam bath for 1 hour, and evaporated to dryness under reduced pressure, and the oily residue was triturated with diethyl ether and filtered to remove sodium iodide. The filtrate was chromatographed on silica (Kieselgel 60; 200 g.) and the product was crystallised from ethanol to give 6-methoxy-2,4-bis(trichloromethyl)benzo[1,3]dioxin, m.p. 105°-107° C.

Provenance & Evidence