Dichloromethyl ether

DICHLOROISOPROPYL ETHER see CHLOROHETHYL ETHYL ETHER DICHLORQHETHANE see METHYLENE CHLORIDE DICHLOROMETHYL ETHER see BIS (2-CNLOROMETHYL) ETHER... 

Dicliloroethane, 52 Dichloroethyl ether, 52 Dichloromethane, 52 Dichloromethyl ether, 52 Dichloromethylphenylsilane, 52 Dichloromonofluoromethane, 52 2-(2,4-Dichlorophenoxy) propionic acid, 52 Dichlorophenyl isocyanates, 53... 

In the onginal route to isoflurane, the methyl ether of tnfluoroethanol is made with dimethyl sulfate [.S] followed by careful chlorination of the methyl group to make the dichloromethyl ether. This ether is fluorinated with hydrogen fluoride and an antimony catalyst and the final step is monochlorination of the a carbon of the ethyl group [S] (equation 2)... 

While the Friedel-Crafts acylation is a general method for the preparation of aryl ketones, and of wide scope, there is no equivalently versatile reaction for the preparation of aryl aldehydes. There are various formylation procedures known, each of limited scope. In addition to the reactions outlined above, there is the Vdsmeier reaction, the Reimer-Tiemann reaction, and the Rieche formylation reaction The latter is the reaction of aromatic compounds with 1,1-dichloromethyl ether as formylating agent in the presence of a Lewis acid catalyst. This procedure has recently gained much importance. 

Chloro-2,2,2-trifluoroethyl dichloromethyl ether Hydrogen fluoride... 

Formylation of aromatic hydrocarbons to aldehydes with dichloromethyl ether 47, 2... 

Many specific examples of these reactions can be found in reviews in the Organic Reactions series.65 Dichloromethyl ethers are also precursors of the formyl group via alkylation catalyzed by SnCl4 or TiCl4.66 The dichloromethyl group is hydrolyzed to a formyl group. 

Dichloro-a-methylbenzhydrol, bl69 yy/w-Dichloromethyl ether, tl65a... 

Tabushi reported that dichlorocarbene CC12 reacts with benzyl alcohol to form an O-H insertion product, i.e., benzyl dichloromethyl ether as the primary product, which undergoes a further base-catalyzed elimination reaction to give benzyl chloride as the final product (Scheme 3, Eq. I).14 In contrast to this... 

Nevertheless, another possibility remained for the formation of insertion products, that they might be formed from the O-H insertion product, e.g., dichloromethyl benzyl ether 5, by the Wittig rearrangement of dichloromethoxy-carbanion 4, (Scheme 5, Eq. I).17 However, treatment of independently prepared benzyl dichloromethyl ether 5 with the same base solely gave benzyl chloride, but the insertion product was not obtained (Eq. 2). Hence, a Wittig-type rearrangement process was excluded. 

Synonyms BCME Bis(chloromethyl) ether Bis-CME BRN 1679223 CCRIS 90 Chloro-(chloromethoxy)methane Chloromethyl ether Dimethyl-l,l -dichloroether sj/ 3-Dichlorodimeth-yl ether Dichloromethyl ether EINECS 208-832-8 Oxybis(chloroethane) RCRA waste number P016 UN 2249. 

Chemical/Physical. Reacts rapidly with water forming HCl and formaldehyde (Fishbein, 1979 Ton et al., 1974). Ton et al. (1974) reported a hydrolysis half-life of 38 sec for sj/ 3-dichloromethyl ether at 20 °C. 

Anticipated products from the reaction of sym-dichloromethyl ether with ozone or OH radicals in the atmosphere, excluding the decomposition products formaldehyde and HCl, are chloromethyl formate and formyl chloride (Cupitt, 1980). 

Source 5// -Dichloromethyl ether may form as an intermediate by-product when form aldehyde reacts with chloride ions under acidic conditions (Frankel et al, 1974 Ton and Kallos, 1974a Travenius, 1982). Tou and Kallos (1974) reported that the reactants (formaldehyde and chloride ions) must be in concentrations of mg/L to form 5// -dichloromethyl ether at concentrations of pg/L. 

Chloromethyl methyl ether may contain 1 to 8% 57/ -dichloromethyl ether as an impurity (Environment Canada, 1993a). 

Formaldehyde reacted with hydrogen chloride in moist air to form 5ym-dichloromethyl ether. This compound may also form from an acidic solution containing chloride ions and formaldehyde (Frankel et al, 1974 Travenius, 1982). In an aqueous solution at 25 °C, nearly all the formaldehyde added is hydrated forming a gem-diol (Bell and McDougall, 1960). May polymerize in an aqueous solution to trio methylene (Hartley and Kidd, 1987). 

Bis(chloromethyl) ether, see sjm-Dichloromethyl ether Bis(2-chloro-l-methylethyl) ether, see Bis(2-chloroiso-propyl) ether... 

Bis-CME, see s/m-Dichloromethyl ether Bis-0,0-diethyl phosphoric anhydride, see Tetraethyl pyrophosphate... 

Chloro-3-hydrox34oluene, see p-Chloro-ro-cresol 2-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether p-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether Chloromethane, see Methyl chloride (Chloromethyl)benzene, see Benzyl chloride Chloromethyl bromide, see Bromochloromethane Chloromethyl ether, see sym-Dichloromethyl ether (Chloromethyl)ethylene oxide, see Epichlorohydrin (2-Chloro-l-methylethyl) ether, see Bis(2-chloroisoprop-yl)... 

Dichloroethyl formal, see Bis(2-chloroethoxy)methane Dichlorodiethyl methylal, see Bis(2-chloroethoxy)methane Dichlorodiisopropyl ether, see Bis(2-chloroisopropyl) ether sjm-Dichlorodimethyl ether, see sj jn-Dichloromethyl ether Dichlorodimethylhydantoin, see l,3-Dichloro-5,5-di-... 

Dichloromethane, see Methylene chloride Dichloromethyl ether, see sjm-Dichloromethyl ether Dichloromethylmethane, see 1,1-Dichloroethane Dichloromonoflnoromethane, see Dichloroflnoromethane... 

Dimethyl-2.2-dichloroethenyl phosphate, see Dichlorvos Dimethyl-1,1 -dichloroether, see s//n-Dichloromethyl ether... 

Oxitol, see 2-Ethoxyethanol Oxitol acetate, see 2-Ethoxyethyl acetate 2-Oxobornane, see Camphor Oxocyclohexane, see Cyclohexanone Oxolane, see Tetrahydrofuran Oxomethane, see Formaldehyde Oxybenzene, see Phenol 1,1 Oxybisbenzene, see Phenyl ether l,l -Oxybis(2-chloroethane), see Bis(2-chloroethyl) ether Oxybis(chloromethane), see s/m-Dichloromethyl ether 2,2 -Oxybis(l-chloropropane), see Bis(2-chloroisopropyl) ether... 

Bis(2-chloroisopropyl) ether Chloromethyl formate, see sjm-Dichloromethyl ether 1 Chloro-2-methylnaphthalene, see 2-Methylnaphthalene... 

Acrylonitrile, Alachlor. Allyl chloride, Allyl alcohol. Benzene, Butane, Chloroethane, Cyclohexene, Chloroprene, Cvclonentene. Dazomet. 1,1-Dichloroethylene, s/m-Dichloromethyl ether, Dimethylamine, A,lV-Dimethylaniline, 2,3-Dimethylbutane, 1,4-Dioxane, Epichlorohydrin,... 

Carbon tetrachloride. Chloroform, 2-Chlorophenol, Cyclohexanol, Cyclopentene, 1,1-Dichloroethylene, irans-l, 2-Dichloroethylene, IV.yV-Dimethylaniline, lV,lV-Dimethylformamide, 2,4-Dimethylphenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Ethyl formate. Formaldehyde, Glycine, Methanol, Methylene chloride. Methyl formate, 2-Methvlphenol. Monuron, 4-Nitrophenol, Oxalic acid, Parathion, Pentachlorophenol, Phenol, l idine. Styrene, Trichloroethylene, Vinyl chloride Formylacetic acid, see cis-l,3-Dichloropropylene, irans-1,3-Dichloropropylene IV-Formylcarbamate of 1-naphthol, see Carbaryl Formyl chloride, see Chloroethane, Chloroform, sym-Dichloromethyl ether, ds-1,3-Dichloropropylene, irans-ES-Dichloropropylene, Methyl chloride. Methylene chloride. Trichloroethylene, Vinyl chloride lV-Formyl-4-chloro-o-toluidine, see Chlornhenamidine. 

Hydracrylic acid, see p-Propiolactone Hydrazobenzene, see Aniline Hydriodic acid, see Methyl iodide Hydrobromic acid, see Bromodichloromethane, Bromoform, Methyl bromide, Metobromuron Hydrochloric acid, see Alachlor. Aldrin, Benzyl chloride, a-BHC, p-BHC, Bis (2-chloroethyl) ether, Bis(2-chloroisopropyl) ether, Bromacil. Bromodichloromethane, Carbon tetrachloride, Chloroethane, Chloroform, o-Chloronitrobenzene. Chloropicrin, Chloroprene, p-Chloronitrobenzene, 2,4-D, see Dalanon-sodium. p.p -DDD, p,p -DDT, Dicamba. 1,1-Dichloroethane, 1,1-Dichloroethylene, fratts-l,2-Dichloroethylene, s/m-Dichloromethyl ether, 2.3-Dichloronitrobenzene. 3.4-Dichloronitrobenzene. 1,2-Dichloropropane, cis-1,3-... 

---