chloromethyl dichloromethyl ether

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Properties of substance:

chloromethyl dichloromethyl ether

Synonyms:

dichloro(chloromethoxy)methane

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₂H₃Cl₃O

Structural formula as text:

ClCH2OCHCl2

Synthesis 1:

Reference: Evans, L., & Gray, R. Preparation of Certain Polychlorodimethyl Ethers / Journal of Organic Chemistry. - 1958. - Vol. 23, No. 5 pp. 746 [doi: 10.1021/jo01099a602]

CH₃OCHCl₂ + Cl₂ → ClCH₂OCHCl₂ + HCl

A 2-liter, 3-necked flask which was equipped with a mechanical stirrer, condenser and ice trap, thermometer, and sintered-glass disk inlet tube was charged with 196 g. (1.7 moles) dichloromethyl methyl ether and 616 g. (4.0 moles) carbon tetrachloride. After heating to reflux, Chlorine was admitted at a rate of 275 ml./min. until 64 g. (0.90 mole) had been introduced. Only initial heating was necessary to hold the temperature at reflux. Upon fractionation, 109 g. (0.73 mole) (81.1% yield) of chloromethyl dichloromethyl ether was obtained with b.p. 128—129°, n(20, D) 1.4630, and d(30/4) 1.464. No methyl trichloromethyl ether was isolated. The physical constants and analysis of this product agreed well with those obtained by the chlorination of bis(chloromethyl) ether.

Synthesis 2:

Reference: Evans, L., & Gray, R. Preparation of Certain Polychlorodimethyl Ethers / Journal of Organic Chemistry. - 1958. - Vol. 23, No. 5 pp. 746 [doi: 10.1021/jo01099a602]

ClCH₂OCH₂Cl + Cl₂ → ClCH₂OCHCl₂ + HCl

A 2-liter, 3-necked flask which was equipped with a mechanical stirrer, condenser and ice trap, thermometer, and sintered-glass disk inlet tube was charged with 460 g. (4.0 moles) bis(chloromethyl) ether and 1232 g. (8.0 moles) carbon tetrachloride. After heating to reflux, chlorine was passed in at a rate of 407 ml./min. until 212 g. (2.98 moles) had been introduced. The heat of reaction maintained the system at reflux. Fractionation of the product yielded 190 g. (1.27 moles) (42.6% yield) of chloromethyl dichloromethyl ether with b.p. 129°, n(20, D) 1.4622 and d(30/4) 1.464.

Anal. Calcd. for CICH2OCHCl2: mol. wt., 149.4; Cl, 71.19. Found: mol. wt., 150; Cl, 70.5.

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