Synthesis of dichloromethyl methyl ether

Preparation of dichloromethyl methyl ether

Preparation of dichloromethyl methyl ether

Preparation of dichloromethyl methyl ether

832 g (4.0 moles) of phosphorus pentachloride and 250 ml of phosphorus oxychloride are stirred together in a 2-liter three-necked flask fitted with a stirrer, reflux condenser, and dropping funnel. 272 ml (4.4 moles) of methyl formate are dropped in within 105 min, with cooling in ice-water such that the inner temperature is kept at 10-20° C. After the addition, stirring is continued at an inner temperature of not more than 30° C until all the phosphorus pentachloride has dissolved (ca. 1 hour). Then the stirrer is removed, the reflux condenser is replaced by a descending condenser, and the obtained reaction mixture is distilled at 80-120 mm (bath at 50-60°) into a receiver cooled to —10° to —15°. The distillate is redistilled through a column, 90 cm in length and 30 mm in diameter, fitted with an evacuated mantle and filled with Raschig rings (5×5 mm), yielding a reflux ratio of 1:10. The 80-100° fraction is fractionated once more in the same way, whereupon dichloromethyl methyl ether, nD 1.4303 at 20°C, passes over between 83° and 85.5° in 77-79.5% yield (353-363 g).

H. Gross, A. Rieche, E. Hoft, E. Beyer, Org. Syn., 47, 47 (1967).

IUPAC Name

dichloro(methoxy)methane

InChI

InChI=1S/C2H4Cl2O/c1-5-2(3)4/h2H,1H3

InChI Key

GRTGGSXWHGKRSB-UHFFFAOYSA-N

Canonical SMILES

COC(Cl)Cl

Depositor-Supplied Synonyms

Dichloromethyl methyl ether, 4885-02-3, 1,1-Dichlorodimethyl ether, Dichloromethoxymethane, dichloro(methoxy)methane, Methane, dichloromethoxy-, Ether, dichloromethyl methyl, alpha,alpha-Dichloromethyl methyl ether, Methoxydichloromethane, 1,1-DICHLOROMETHYL METHYL ETHER, (Dichloromethyl)methyl ether, .alpha.,.alpha.-Dichloromethyl methyl ether, alpha,alpha-Dichloromethyl ether, EINECS 225-498-9, NSC 91480, BRN 1900293, dichloromethoxy methane, PubChem2376, CH3OCHCl2, dichloromethylmethylether, dichloro-methoxy-methane, methoxymethylene chloride, dichloromethylmethyl ether, AC1L2HFF, Dichloromethyl methylether, 1,1-Dichlorodimethylether, dichioromethyl methyl ether, dichloromethyl-methyl ether, WLN: GYGO1, ACMC-2097gi, asym-Dichlorodimethyl Ether, AC1Q3H3I, SCHEMBL62080, (dichloromethyl)-methyl ether, D65658_ALDRICH, KSC490I8N, Methyl (dichloromethyl) ether, 1,1-dichloro-1-methoxymethane, DTXSID2063636, CTK3J0486, NSC91480, ZINC4261782, ANW-13936, MFCD00000828, NSC-91480, .alpha.,.alpha.-Dichloromethyl ether, AKOS009158601, 5-NITROFURFURYL ALCOHOL, TECH., LS00123, MCULE-7296291650, VZ35676, AK111136, LS-67819, OR010919, SC-04782, KB-201001, KB-251342, TR-017740, D1645, FT-0624719, LT00067771, X5964, K-0073, InChI=1/C2H4Cl2O/c1-5-2(3)4/h2H,1H, I14-19010, F0001-1278

Removed Synonyms

Octyl hexanoate, C2H4Cl2O, , -Dichloromethyl methyl ether, 1,1-Dichloromethylmethyl ether, GRTGGSXWHGKRSB-UHFFFAOYSA-N, MolPort-003-930-857, CID21004, RTR-017740

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