Synthesis of polychloro compounds with aluminium chloride XIII. The condensation of formaldehyde, symm.‐dichlorodimethyl ether, and chloromethyl methyl ether with trichloroethene and with tetrachloroethene

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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.

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