The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Chloroethyl acetate( cas:542-58-5 ) is researched.Category: chiral-catalyst.Mastagli, Pierre; De Nanteuil, Michel published the article 《Reaction of titanium tetrachloride with ketone [ethylene ketals]》 about this compound( cas:542-58-5 ) in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques. Keywords: acetal titanium tetrachloride reaction; dioxolane titanium tetrachloride reaction; titanium tetrachloride acetal reaction. Let’s learn more about this compound (cas:542-58-5).
TiCl4 attacks cyclohexanone ethylene ketal (I, RR1 = cyclohexyl) (Ia) to give 2-chloroethyl 6-(1-cyclohexen-1-yl)caproate (II). This reaction was extended to several cyclic and linear ketone ethylene ketals. TiCl4 effects a kind of oxidation-reduction on 2 mols. of ethylene ketal leading to an ester and an alkene according to the general equation: I (R = R7CH2, R1 = R2) →R2CO2CH2CH2Cl (III) + R1CH:CR2CH2R1. The alc. part of III arises from the glycol forming the dioxolane ring. A cyclic ketone gives an olefinic ester. The mechanism of the reaction was not determined The exptl. results are summarized in the table; also IV gave 30% II by the same procedure. Thus, 0.5 mole TiCl4 was added dropwise to 1 mole ketal in CH2Cl2 with ice-bath cooling, kept overnight, hydrolyzed, washed with H2O, and distilled Characterization of the esters marked (a) in the table was made by reaction of the corresponding Et ester with ClCH2CH2OH in the presence of (PrO)4Ti; those marked (b) by esterification of the corresponding acid with ClCH2CH2OH; and those marked (c) by IR and N.M.R. anal. In the reaction of TiCl4 with acetone ethylene ketal, AcOCH2CH2Cl was obtained, but the formation of isobutene was not demonstrated since it forms high polymers in the presence of Lewis acids.
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