The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Action of aluminum chloride on esters of polyatomic alcohols》. Authors are Dobryanskii, A. F.; Sivertsev, A. P..The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Recommanded Product: 2-Chloroethyl acetate. Through the article, more information about this compound (cas:542-58-5) is conveyed.
Reaction of AlCl3 with esters of polyat. alcs. leads to replacement of only part of the acyl groups by Cl; usually 1 acyl group is left and does not react with AlCl3. The following esters do not react with AlCl3: AcOCH2CH2Cl, BzOCH2CH2Cl, AcOCH2CHClCH2Cl, and AcOCH2C(CH2Cl)3. This is explainable by accumulation of neg. Cl atoms in such esters. In the course of the reaction AlCl3 is changed into ClAl(OAcyl)2. (CH2OAc)2 (60 g.) and AlCl3 (47.8 g.) 1 hr. at 150-60° gave 38.5 g. distillable oil, which on redistillation gave a fraction b. 142-8°, d2020 1.1295, identified as AcOCH2CH2Cl; the Al compound was best isolated by boiling 6 g. (CH2OAc)2 and 5 g. AlCl3 in 60 cc. CCl4 1 hr., followed by cooling and separation of the glassy layer, which was powdered in dry benzene and washed with Et2O; its analysis corresponded to C4H6O4AlCl. (CH2OBz)2 (20 g.) and 10.5 g. AlCl3 heated 1 hr. to 150-60° gave 108 g. oil, which on distillation gave a fraction b40 139-40°, d2020 1.1783, d420 1.1789, nD20 1.5283, identified as BzOCH2CH2Cl; heating 5.6 g. (CH2OBz)2 and 1.3 g. AlCl3 1 hr. at 150°, followed by cooling and separation of the crystals, gave the Al compound in pure state after washing as above, and its analysis corresponded to C14H10O4AlCl. Triacetin (219 g.), 44.5 g. AlCl3, and 323 g. CCl4 boiled 1 hr. gave 160 g. of oil which on distillation gave a fraction b20 125-30°, d2020 1.2018, d420 1.1996, nD20 1.4393, identified as diacetin chlorohydrin (diacetoxychloropropane); the AlCl3 under such conditions is transformed into C4H6O4AlCl, which was isolated by cooling a mixture of 10.8 g. triacetin and 6.6 g. AlCl3 which had been heated 1 hr. to 150°. Triacetin (108 g.) and 66.7 g. AlCl3 heated 1 hr. to 140-50° gave 104.4 g. oil, which on distillation gave a fraction b20 90-5°, b40 115-20°, d2020 1.2733, d420 1.2714, identified as 2,3-dichloropropyl acetate; refluxing 20 g. of this with 60 g. NaI and 300 cc. Me2CO, then heating in a sealed tube to 120°, gave the diiodide which with Zn gave 5.6 g. allyl acetate, b. 99-104°, d420 0.9941, nD20 1.4045. Pentaerythritol tetraacetate (I) (30.4 g.) and 7.3 g. AlCl3 heated 1 hr. at 160° gave 26.5 g. oil which on distillation gave a fraction b4.5 152-60°, d2020 1.2272, d420 1.225, nD20 1.4587, identified as pentaerythritol triacetate monochlorohydrin. I (30.4 g.) and 13.3 g. AlCl3 heated 1 hr. at 160° gave 26.7 g. oil which on distillation gave pentaerythritol diacetate dichlorohydrin, b6 146-8°, d2020 1.2620, d420 1.2600, nD20 1.4681. I (30.4 g.) and 26.7 g. AlCl3 heated 1 hr. to 150-60° gave pentaerythritol monoacetate trichlorohydrin, b8 126-7°, d2020 1.3111, d420 1.3057, nD20 1.4832. The Al salt which separated as a crust from the cooled mixture, after washing with Et2O analyzed well for C4H6O4AlCl.
I hope my short article helps more people learn about this compound(2-Chloroethyl acetate)Recommanded Product: 2-Chloroethyl acetate. Apart from the compound(542-58-5), you can read my other articles to know other related compounds.