The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《New preparation and some reactions of di(β-chloroethyl) sulfate》. Authors are Suter, C. M.; Evans, Peter B..The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Computed Properties of C4H7ClO2. Through the article, more information about this compound (cas:542-58-5) is conveyed.
Distillation of 100 g. (ClCH2CH2)2O and 48.4 g. of SO3 at 2-3 mm. gives 91% (102 g.) of (ClCH2CH2)2SO4 (I), b3 126-9°; if the I is stirred with warm dilute alkali before the 2nd distillation the ester remains water-white indefinitely. Refluxing 20 g. I, 7.5 g. AcONa and 15 cc. AcOH for 1 h. gives 95.5% of ClCH2CH2OAc; BzONa and I, heated 2 h. at 170°, give 61.5% of ClCH2CH2OBz. I (0.112 mol.) and the Grignard reagent from 0.075 mol. PhCH2Cl give 66% of Ph(CH2)3Cl; PhMgBr gives 25% of Ph(CH2)2Cl. Various other reactions are discussed. (BrCH2CH2)2O gives a low yield of I. Attempts to obtain sulfates from Pr2O and (ClCH2CH2CH2)2O gave tarry reaction mixtures which could not be distilled even in a high vacuum.
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