3-(2,2,2-Trichloro-1-acetoxy-ethoxy)-toluene → 1-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

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Reaction Steps

By a metallic reductive dehydrohalogenation method. 1(3-tolyloxy)-2,2,2-trichloroethyl acetate (14.2 g) was dissolved in glacial acetic acid (40 ml) and zinc dust (3.6 g) was slowly added to the solution with stirring at the ambient temperature. The temperature rose to 60° C in response to the exothermic reaction which occurred, after which the mixture was heated at 50°-60° C for 4 hours. The mixture was filtered and the filtrate poured in an excess of water and extracted with chloroform. The extracts were washed twice with water, with saturated sodium bicarbonate solution, and finally with water. After drying the chloroform extracts over anhydrous magnesium sulphate, the solvent was removed by evaporation under reduced pressure and the residual oil distilled to yield crude 3-tolyl 2,2-dichlorovinyl ether, collected as a fraction boiling at 92°-95° C/0.3 mm, which was redistilled and the fraction boiling at 84° C/0.2 mm Hg collected.

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