Butyl 1-chloroethyl ether

The preparation of butyl 1-chloroethyl ether is described in detail in Synthesen organischer Verbindungen 203... 

Bis-(2-methoxyethyl) ether, 2549 f 1,3-Butadiene, 1480 f 1,3-Butadiyne, 1385 f 2-Butanol, 1695 f Buten-3-yne, 1423 f Butyl ethyl ether, 2540 f Butyl vinyl ether, 2484 f 2-Chloro-1,3-butadiene, 1451 f Chloroethylene, 0730 f 2-Chloroethyl vinyl ether, 1557... 

Note May contain acetic acid, 2-methyl-l,3-dioxolane, and bis(2-chloroethyl) ether as impurities. May be inhibited with butylated hydroxytoluene. 

Diffiuex investigated a synthesis of cyclic poly(vinyl ether) using cationic polymerization [26,28]. The reaction process is depicted in Fig. 9. They studied on the living cationic polymerization of 2-chloroethyl vinyl ether (CEVE) initiated with the HI adduct of 4-(vinylbenzyloxy)butyl vinyl ether prepared by reacting chloromethyl styrene with sodium salt of 4-hydroxy-butyl vinyl ether in THF at 80 °C. By the cationic polymerization of CEVE, o /o-hetcrofunclional linear polymer precursor of cyclic poly(CEVE) was produced. The MWDs of the polymers were unimodal and very narrow (< 1.2),... 

Ethyldioxane (IJ) was a product of the reaction of p-dioxane with ethylene in the presence of hydrochloric acid and di-t-butyl peroxide at 130-140 C (Expts. 29 and 30). However, the major product was bis-(2-chloroethyl) ether ( ) and a smaller amount of... 

The synthesis of block copolymers of styrene - 2-chloroethyl vinyl ether [307], p-methoxystyrene - i-butyl vinyl ether... 

Triblock copolymers using NVK, 4-(l-pyrenyl)butyl vinyl ether and 2-chloroethyl vinyl ether have been synthesized in an sequential cationic polymerization technique." The block copolymers were further functionalized with 2-(4-hydrox)q)henyl)-5-phenyl-1,3,4-oxadiazole, by reaction of... 

The method has been generalized and extended to include the preparation of -propyl-and n-butyl-a-chloroethyl ethers. It was found advisable for the purpose of synthesis to avoid distillation, the yield being diminished as much as 20-25% by a single fractionation. The upper ethereal layer was removed and dried over calcium chloride. For the a-chloroethyl ethers mentioned, the yield varies from 80 to 90% of crude or 60 to 69% of the distilled product. 

The alkyl-Q -chloroethyl ethers were brominated. The crude reaction product may be submitted directly to distillation under diminished pressure, but it was found advisable in this case to avoid distillation. The hydrogen chloride was removed under diminished pressure or by aspirating a slow current of air through the reaction mixture. The yields vary from 93 to 95% of crude or 88.5 to 91% of distilled product. For the case of n-butyl-o ,jS-dibromoethyl ether, the yield was 95.2%, b.p. 115°C at 36 mmHg. 

Ether, butyl glycidyl. See Butyl glycidyl ether Ether, butyl vinyl. See n-Butyl vinyl ether Ether chloratus. See Ethyl chloride Ether, 2-chloroethyl vinyl. See,2-Chloroethyl vinyl ether... 

Phosphonic acid, butyl-, dibutyl ester. See Di butyl butyl phosphonate Phosphonic acid, (2-chloroethyl)-bis(2-chloroethyl) ether. See Bis (2-chloroethyl) 2-chloroethylphosphonate Phosphonic acid, dimethyl ester. See. Dimethyl hydrogen phosphite... 

O Brien and King (1949) gave the JVna values at 1 atm for three more ethers but did not give the pna and m data therefore, the Xhci vs Phci plots cannot be drawn from actual data. However, looking at Fig. 92, it appears highly probable that the Pna vs jcho plot would not be linear and certainly the Nhci plot would not be linear if it were assumed that the Xhci plot were linear. For phenetole at 10°C, it is extremely unlikely that the Xhci vs Phci plot would be linear, and the Nhci plot would be clearly separated, as for the chloroethyl ether shown in Fig. 92. The lines for M-butyl phenyl ether would also be clearly distinctive. 

Related Reagents. Benzyl Chloromethyl Sulfide r-Butyl Chloromethyl Ether 2-Chloroethyl Chloromethyl Ether Chloromethyl Methyl Ether Chloromethyl Methyl Sulfide (p-Methoxy-benzyloxy)methyl Chloride 2-Methoxyethoxymethyl Chloride 2-(Trimethylsilyl)ethoxymethyl Chloride. 

In a first report [24], the enantioselectivities of various proteases were evaluated by comparing the biocatalyzedhydrolysis of2-chloroethyl esters of N-acetyl-i- and D-amino acids in water and their transesterification with w-propanol in butyl ether. By comparing the ratio of the kc t/Ku values for the l- and D-enantiomers in the two reactions, a remarkable relation of the proteases enantioselectivity was observed apparently, in this case, the organic solvents destroyed the selectivity of the tested enzymes. This finding... 

Biomomethyl s-butyl ether a-Chloroethyl n-propyl ether... 

Bauld and coworkers have examined the cation radical cycloadditions of 1,3-dienes with electron-rich alkenes and found that, under photosensitized electron-transfer conditions, [2 -i- 2] cycloaddition is in many cases favored over Diels-Alder addition. Thus, as illustrated in equation (30), 1, T-dicyclopentenyl (186) reacts with p-chloroethyl vinyl ether under electron transfer conditions to afford the cyclobutane adduct (187), which was cleaved to the cyclobutanol (188) in 70% yield upon treatment with n-butyl-iithium. Oxyanion-accelerated VCB rearrangement then provided (189) as a mixture of diastereomers in... 

Annelation.1 Use of divinyl ketone, CH2=CHCOCH=CH2, in annelation reactions has the disadvantage that bisalkylation competes with monoalkylation. j8-Chloroethyl vinyl ketone, however, can be used as the synthetic equivalent. Thus the sodium salt of the diketone (1) reacts smoothly with /3-chloroethyl vinyl ether to give the Michael addition product (2), which on dehydrohalogenation in glyme gives (3) in overall yield of 60% (pure). This product reacts with /-butyl... 

Chloroethyl ethyl ether Butyl nitrite Butyl alcohol sec-Butyl alcohol ferf-Butyl alcohol... 

Several studies on the reactivities of small radicals with donor-acceptor monomer pairs have been carried out to provide insight into the mechanism of copolymerizations of donor-acceptor pairs. Tirrell and coworkers " reported on the reaction of n-butyl radicals with mixtures of N-phcnylmalcimidc and various donor monomers e.g. S, 2-chloroethyl vinyl ether),. lenkins and coworkers have examined the reaction of t-butoxy radicals with mixtures of AN and VAc. Both groups have examined the S-AN system (see also Section 7.3.1.2). In each of these donor-acceptor systems only simple (one monomer) adducts are observed. Incorporation of monomers as pairs is not an important pathway i.e. the complex participation model is not applicable). Furthermore, the product mixtures can be predicted on the basis of what is observed in single monomer experiments. The reactivity of the individual monomers (towards initiating radicals) is unaffected by the presence of the other monomer i.e. the complex dissociation model is not applicable). Unless propagating species are shown to behave differently, these results suggest that neither the complex participation nor complex dissociation models apply in these systems. 

Acrylate copolymers produced by emulrion polymerization are being used as elastomers which, after vulcanization, have a combination of heat resistance and oil resistance useful in specialty applications such as gai ts for automatic transmissions in automotive engines. Two t3q>es of copolymers are being used. In one, ethyl acrylate is copolymerized with about 5 per cent of a chloro-containing monomer such as chloroethyl vinyl ether in the other, either ethyl acrylate or butyl acrylate is copolymerized with about 5-15 per cent of acrylonitrile., ... 

Pyrolysis of the 3,3-bis-(2-chloroethoxy)-5cx-androstane derivative (368) gave the A -enol ether (369), which afforded the 2a,3a-methano-derivative (370) with the Simmons-Smith reagent. The 2-chloroethyl group was easily removed by n-butyl-lithium to give the cyclopropanol (371), which rearranged on melting to give the 2a-methyl-3-ketone (372). °... 

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