The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some choline derivatives》. Authors are Hebky, J..The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Reference of 2-Chloroethyl acetate. Through the article, more information about this compound (cas:542-58-5) is conveyed.
The orthoformate (I), orthoacetate (II), and orthophosphate (III) of (2-hydroxyethyl)trimethylammonium chloride were prepared from Me3N (IV) in C6H6 and the appropriate 2-chloroethyl ester and identified as their tripicrates. I, II, and III probably break up in vivo into choline chloride, since biol. tests on rabbits showed they had the same activity as choline chloride, but only 1/1000 that of acetylcholine. 2-Chloroethyl orthoformate (V), a colorless, pleasant-smelling, stable liquid, b14 157° (after redistillation), was obtained in 83.4-g. yield (88.1% theory) by fractionally distilling under reduced pressure 2.5 hrs. a mixture of 55.6 g. (0.376 mol.) of HC(OEt)3 and 180 g. anhydrous CH2ClCH2OH with 1 drop saturated alc. HCl. 2-Chloroethyl orthoacetate (VI), a colorless sweet-smelling liquid turning slightly yellow on standing, b13 155-6°, was formed (18 g.) in a similar manner from 16.25 g. (0.1 mol.) MeC(OEt)3 and 50 g. dry CH2ClCH2OH with 1 drop alc. HCl. V (3 g.) and 15 cc. of a 16.9% C6H6 solution of IV heated 8 hrs. in a sealed tube at 100° formed 2 layers, the bottom one of which was I, a glassy, colorless, hygroscopic mass after removing C6H6, washing with H2O, and drying in a vacuum desiccator over P2O5 1 week. I precipitated from absolute alc. with dry Et2O formed white crystals, m. 280° (decomposition). II, obtained from 4.4 g. VI heated in a sealed tube at 80-90° 10 hrs. with 25 cc. of a 16.9% C6H6 solution of IV and treated like I, had properties similar to I. (ClCH2CH2O)3PO (VII) was prepared according to (B.I.O.S. Final Report Number 696, p. 7) from 50 g. CH2ClCH2OH and 27.3 g. POCl3. The colorless product, dried 3 weeks over fused Na2SO4, weighed 23.3 g. VII (5.7 g.) and 20 cc. of a 21% solution of IV heated 10 hrs. in a sealed tube at 80° gave a thick, colorless sirup which changed into a glassy, slightly milky, almost solid hygroscopic mass of III after removing the benzene and drying in a vacuum desiccator over P2O5 3 months. Addition of Na picrate to a concentrated aqueous solution of I formed the tripicrate, HC[OCH2CH2NMe3C6H2O7N3]3, m. 214° after several recrystallizations from 70% EtOH with added charcoal. The crystalline tripicrate of II, MeC[OCH2CH2NMe3C6H2O7N3]3, formed in a similar way from II, m. 187-9°. The tripicrate, of III, OP[OCH2CH2NMe3C6H2O7N3]3, crystallized after 10 days from a solution of Na picrate added to a concentrated aqueous solution of III, m. 192° (repeated recrystallizations from 70% EtOH).
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