H. Prins
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The condensation of formaldehyde (paraformaldehyde or trioxane) with trichloroethene in the presence of aluminium chloride gives a mixture of 2,3,3,3-tetrachloropropanol-1, the di-ether of this alcohol (2,3,3,3,2′,3′,3′,3′-octochloro-di-n-propylether), and αβ-dichloropropionyl chloride. The same di-ether is obtained by the condensation of symm.-dichlorodimethyl ether with trichloroethene. Condensation of chloromethyl methyl ether with trichloroethene gives the methyl ether of 2,3,3,3-tetrachloropropanol-1. Tetrachloroethene yields, by condensation with formaldehyde, 2,2,3,3,3-pentachloropropanol-1 and the di-ether of this alcohol (2,2,3,3,3,2′,2′,3′,3′,3′-decachloro-di-n-propylether). The same ether results from the condensation of tetrachloroethene with symm.-dichlorodimethyl ether. At temperatures above 50°, cleavage and dehydrohalogenation of the di-ether of 2,2,3,3,3-pentachloropropanol-1 occurs, with formation of 1,1,2,3,3-pentachloropropene-1 as well as 2,2,3,3,3-pentachloropropanol-1. Condensation of chloromethyl methyl ether with tetrachloroethene is accompanied by cleavage of the ensuing methyl ether of 2,2,3,3,3-pentachloropropanol-1, and yields 2,2,3,3,3-pentachloropropanol-1. The mechanism of these reactions is discussed.