P-chloroethyl alcohol

Synonyms AI3-52326 BRN 0878139 CCRIS 859 2-Chloroethanol 5-Chloroethanol 2-Chloroethyl alcohol p-Chloroethyl alcohol EINECS 203-457-7 Ethylene chlorhydrin Glycol chlorohydrin Glycol monochlorohydrin 2-Hydroxyethyl chloride 2-Monochloroethanol NCI-C50135 UN 1135. 

Chloroethyl alcohol, see Ethylene chlorohydrin p-Chloroethyl alcohol, see Ethylene chlorohydrin Chloroethylene, see Vinyl chloride... 

Synonyms P-Chloroethyl alcohol glycol chlorohydrin 2-chloroethanol... 

SYNS AETHYLENECHLORHYDRIN (GERMAN) 2-CHLOORETHANOL (DUTCH) 2-CHLORAETHANOL (GERMAN) 2-CHLORETHANOL (GERMAN) A-CHLOROETHANOL 2-CHLOROETHANOL (M.AK) P-CHLOROETHYL ALCOHOL 2-CHLOROETHYL ALCOHOL CHLOROETHYLOWY ALKOHOL (POLISH)... 

Chloro-1-(3-ethoxy4-nitrophenoxy)-4-(trifluoromethyl) benzene. See Ox luorfen 2-Chloroethyl alcohol p-Chloroethyl alcohol. See Ethylene chlorohydrin 2-Chloroethylamine hydrochloride CAS 870-24-6 EINECS/ELINCS 212-793-2 Synonyms 2-Aminoethyl chloride hydrochloride p-Chloroethylamine hydrochloride 2-Chloroethylammonium chloride... 

P-Chloroethyl alcohol Ethylchlorohydrin Ethylene chlorhydrin Ethylene glycol, chlorohydrin Glycol chlorohydrin Glycolmonochlorhydrin Glycol monochlorohydrin 2-Hydroxyethyl chloride 2-Monochloroethanol Empirical C2H5CIO Formula CICH2CH2OH... 

An interesting variation of this reaction that made use of a three-component, one-pot solventless procedure with the corresponding trialkyl phosphites gave dramatically improved yields of many heterosubstituted glyphosate phosphonate diesters (37). When exactly one equivalent of water, 25, and tris-p-chloroethyl phosphite were mixed and heated under neat conditions for a few hours, nearly quantitative yields of displaced p-chloroethanol and the desired triester product 27 were obtained. If desired, the displaced alcohol was first removed by vacuum distillation, or the mixture could be hydrolyzed directly to GLYH3. Various oxygen, sulfur, nitrogen, cyano, and carboxylate functionalities were similarly accommodated in the trialkyl phosphite. 

The product is 2-phenyl-2-(l-hydroxycyclopentyl)ethanoic acid, melting at 95° to 97°C. Of this product, 4.5 g in 30 cc of dry isopropyl alcohol are refluxed for 16 hours with 2.5 g of p-chloroethyl dimethyl amine. The solution is cooled and filtered clear from the solid by-product. The solvent is removed under reduced pressure on the steam bath and the residue is washed with anhydrous ether. It is dissolved in ethyl acetate from which it crystallizes. It is the hydrochloride of p-(dimethylamino)ethyl ester of 2-phenyl-2-(l-hydroxycyclopentyl) ethanoic acid, melting at 134° to 136°C. 

A solution of 8 g of ethylene chlorohydrin and 10.2 g of triethylamine in 50 cc of absolute dioxane is slowly added dropwise to a solution of 25.9 g of N,N-bis-(p-chloroethyl)-phosphoric acid amide dichloride in 100 cc of absolute dioxane. The mixture is then heated for 2 hours at 60°C. After cooling, a solution of 7.5 g of 1,3-propanolamine and 10.2 g of triethylamine in 50 cc of absolute dioxane is added dropwise while stirring well and at a temperature up to 30°C. The mixture is left to stand for another 12 hours. The liquid is filtered off with suction from the precipitated triethyamine hydrochloride. The filtrate is filtered through carbon and concentrated by evaporation in water-jet vacuum at 40°C. The residue is dissolved in a little alcohol. Copious amounts... 

Synonyms Chloroethanol 2-Chloroethanol 2-Chloro-1-ethanol P-Chloroethanol 2-Chloroethyl alcohol... 

An excerpt from a synthesis of the phytosiderophore Nicotianamine illustrates the formation and cleavage of the 2,2,2-trichloroethyl carbonate protecting group [Scheme 4.357].676 Reaction of alcohol 357,1 with 2,2,2-trichloroethyl chloroformate and a catalytic amount of DMAP in pyridine gave the 2,2>2-tri-chloroethyl carbonate 357 2 in 98% yield. After oxidative destruction of the two p-methoxyphenyl rings to carboxylic acids and esterification, the 2224ri-chloroethyl carbonate 3573 was cleaved with zinc and acetic acid in 97% yield. 

Lithium bis(trimethylsilyl)amide (2.50 mmol, 1.0 M in THF) was added dropwise to a solution of l,4-dimethoxy-2-hydroxymethylnaphthalene (2.29mmol) dissolved in 10 ml THF at —78°C. This was then added dropwise to a solution of bis(2-chloroethyl)phosphoramidic dichloride (2.75 mmol) dissolved in 20 ml THF, the reaction mixture stirred at —78°C 90 minutes, warmed to —20°C, and ammonia passed through the mixture 10 minutes. Thereafter, the mixture stirred an additional 10 minutes, 30 ml 2% HCl added, and then extracted 4 times with EtOAc. The combined organic layers were washed twice with saturated brine, dried, filtered, and evaporated. The mixture was purified by chromatography using methyl alcohol/EtOAc, 2 98, and the product isolated in 50% yield as a yellow oil, Rf = 0.59. H- and P-NMR data supplied. 

Later, it was reported [69] that the alcohols 136a, 136n, 136o, and 136p gave upon treatment with di-(2-chloroethyl)dichloroselenurane (139) at 70 °C the corresponding chlorides 138a and 138 n-p in yields between 8 and 34% (Eq. 32). 

Ethylbenzyl chloride Ethylene dibromide V,V -Dinitroethylenediamine Hexaethyl tetraphosphate M ethylbenzyl alcohol m-Benzenedisulfonic acid Methylbenzyl chloride V-Bromosuccinimide Octamethyl pyrophosphoramide p-Aminosalicylic acid Pentaerythritol tetranitrate Tris-(/3-chloroethyl) amine Tetraethylammonium bromide Tetraethyl pyrophosphate 2,2,6,6-Tetramethylolcyclohexanol... 

Nucleophilic participation is important only for esters of alcohols that have p/f < 13. Specifically, phenyl and trifluoroethyl esters exhibit nucleophilic catalysis, but methyl and 2-chloroethyl esters do not. This result reflects the fate of the tetrahedral intermediate that results from nucleophilic participation. For relatively acidic alcohols, the alkoxide group can be eliminated, leading to hydrolysis via nucleophilic catalysis. 

Tris-(2-ethoxyethyl)amine 734 A solution of potassium hydroxide (6.24 g, 0.11 mole) in 95 % ethanol (25 ml) is heated with tris-(2-chloroethyl)ammonium chloride for 3 h under reflux. The precipitated sodum chloride is filtered off, the alcoholic solution is evaporated at 10 mm, and the residue is dissolved in water. The solution is extracted with ether, and the extract is dried over magnesium sulfate and distilled, giving tris-(2-ethoxyethyl)amine, (ROCH2CH2)3N (2.80 g, 66%), b.p. 134-137°/l2 mm (hydrochloride, m.p. 193-195°). 

Alkyl benzenesulfonates 686 20-30% sodium hydroxide solution is added dropwise, with vigorous shaking, to benzenesulfonyl chloride (1 part) and the alcohol (1 part), until the alkaline reaction is permanent after considerable shaking and the oil that separates is completely free from chlorine. Benzene and water are added, the two layers are separated, the organic layer is washed and dried, and the solvent and alcohol are removed in a vacuum by means of a water-bath at 30-40° (not higher). This process has afforded the allyl (explosive decomposition on distillation), 2-chloroethyl, b.p. 184°/9mm, 2-bromoethyl, b.p. 185-187°/ 16 mm, and 2-chloro-l-(chloromethyl)ethyl ester, b.p. 200-205°/20 mm, m.p. 50° (from benzene). 

In general, naturally occurring (IV-protected) L-amino acid esters of short-chain alcohols, such as methyl and ethyl esters are usually sufficiently reactive as acceptors to achieve reasonable reaction rates in enzymatic peptide synthesis via aminolysis. For less reactive (nonnatural) analogs, such as a-substituted [313] or D-configured amino acids [314], activated esters are recommended, among them, 2-haloethyl (e.g., 2-chloroethyl, trifluoroethyl) [315], p-nitrophenyl [316], or guanidinophenyl esters [317]. For the use of cyclic activated esters [5(47/)-oxazolones] see below. 

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