Ethyl ferf-butyl ether

CoHuO ferf-Butyl ethyl ether 73 Nonazeotrope 106... 

A student attempted to prepare ferf-butyl ethyl ether by a substitution reaction between 2-chloro-2-methylpropane (ferf-butyl chloride) and sodium ethoxide. None of the desired ether was obtained. What product was formed and why did this route to the ether fail Suggest a different substitution reaction that should yield the desired product. 

Krahenbuhl, M.A., Gmehling, J. (1994) Vapor pressure of methyl fert-butyl ether, ethyl fert-butyl ether, isopropyl tert-butyl ether, fert-amyl methyl ether, and ferf-amyl ethyl ether. J. Chem. Eng. Data 39, 759-762. 

By keeping the above in mind, the following three series of solvent systems can provide an ideal range of the K values for a variety of samples w-hexane/ethyl cetate/n-butanol/methanol/water, chloroform/metha-nol/water, and ferf-butyl methyl ether/butanol/acetonito-rile/water. 

For the sample mixmre with an unknown composition, the search for the suitable two-phase solvent system may be initiated with the partition coefficient measurement with n-hexane/ethyl acetate/n-butanol/methanol/water (5 5 0 5 5) (Table 1), chloroform/methanol/water (10 3 7) (Table 2) or ferf-butyl methyl ether/butanol/ acetonitorile/water (6 0 3 8) (Table 3). If the Ai(org/aq) value is too large, the search should be directed toward the more hydrophobic solvent systems and, if the K value is too small, the search should be directed toward the more hydrophilic solvent systems until the proper K values are obtained. 

Subsequent collapse of the packing can be prevented by pumping about 0.51 of solvent through at this maximum pressure level, that used later for chromatography being perfectly adequate. A silica column should be equilibrated with an eluotropic series of solvents (e.g. methanol ethyl acetate —> ferf-butyl-methyl ether —> hexane) if the slurry has been topped up with water. Finally, the column... 

If, however, you want to synthesize tert-butyl ethyl ether, the starting materials must be an ethyl halide and ferf-butoxide ion. If you tried to use a tert-butyl halide and ethoxide ion as reactants, you would obtain the elimination product and little or no ether because the reaction of a tertiary alkyl halide under Sn2/E2 conditions forms primarily the elimination product. So, in carrying out a Williamson ether synthesis, the... 

Chemists almost invariably use common names for low-molecular-weight ethers. For example, although ethoxyethane is the lUPAC name for CH3CH2OCH2CH3, it is rarely called that, but rather is called diethyl ether, ethyl ether, or, even more commonly, simply ether. The abbreviation for ferf-butyl methyl ether, used at one time as an octane-improving additive to gasolines, is MTBE, after die common name of methyl ferf-butyl ether. 

Steffan RJ, K McClay, S Vainberg, CW Condee, D Zhang (1997) Biodegradation of the gasoline oxygenates methyl ferf-butyl ether, ethyl ferf-butyl ether, and amyl tcrt-butyl ether by propane-oxidizing bacteria. Appl Environ Microbiol 63 4216-4222. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

CASRN 637-92-3 molecular formula CeH O FW 102.17 Chemical/Physical The atmospheric oxidation of ethyl ferf-butyl ether by OH radicals in the presence of nitric oxide yielded ferf-butyl formate as the major product. Minor products included formaldehyde and nitrogen dioxide. In the absence of nitric oxide, 2-ethoxy-2-methylpropanal is likely to form (Wallington and Japar, 1991). 

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