Group of substances:

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

Structural formula as text:

Molar/atomic mass: 114.9586

Boiling point (°C):

Synthesis 1:

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 322 g. (4.0 moles) of chloromethyl methyl ether and 1232 g. (8.0 moles) carbon tetrachloride. The flask was illuminated with a 275-watt ultraviolet bulb. Chlorine was admitted through the sintered disk at a rate of 200 ml./min. until 142 g. (2.0 moles) had been introduced. The heat of reaction maintained the system at reflux. Fractionation of the product produced 163 g. (1.4 moles) bis(chloromethyl) ether; b.p. 103—105°, n(20, D) 1.4421 and 24 g. (0.2 mole) dichloromethyl methyl ether; b.p. 82—84°, n(20, D) 1.4353.

Calcd. for CH3OCHCl2: Sapon. Equiv., 38.3; Cl, 61.68. Found: Sapon. Equiv., 38.4; Cl, 61.77.

Reactions:

1. Yeild 88%. [Ref.1]
   CH₂(COOH)₂ + 2CH₃OCHCl₂ → CH₂(COCl)₂ + 2HCOOCH₃ + 2HCl
   
2. Yeild 92,5%. [Ref.1]
   C₆H₅CH₂COOH + CH₃OCHCl₂ → C₆H₅CH₂COCl + HCOOCH₃ + HCl
   
3. Yeild 88%. [Ref.1]
   CCl₃COOH + CH₃OCHCl₂ → CCl₃COCl + HCOOCH₃ + HCl
   
4. Yeild 61%. [Ref.1]
   2CH₃COOH + CH₃OCHCl₂ + 2(C₂H₅)₃N → (CH₃COO)₂CHOCH₃ + 2(C₂H₅)₃NHCl
   

References:

1. Zeitschrift fur Chemie. - 1978. - Vol. 18, No. 6. - pp. 201-210 [DOI: 10.1002/zfch.19780180602]
   
2. Физер Л., Физер М. Реагенты для органического синтеза. - Т. 5. - М., 1971. - pp. 185 [Russian]
   
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   © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru