Ethyl sulfate process in which ethylene is reacted with sulfuric acid to produce ethyl sulfate followed by hydrolysis, but this method has been mostly replaced by direct hydration of ethylene. Ethyl sulfate can be produced in a laboratory setting by reacting ethanol with sulfuric acid under a gentle boil, while keeping the reaction below 140 °C. The sulfuric acid must be added dropwise or the reaction must be actively cooled because the reaction itself is highly exothermic. If the temperature exceeds 140 °C, the ethyl sulfate product tends to react with residual ethanol starting material, producing diethyl ether. If the temperature exceeds
Ethyl acetoacetate a bidentate ligand. For example, it forms purple coordination complexes with iron(III) salts: Ethyl acetoacetate can also be reduced to ethyl 3-hydroxybutyrate. Ethyl acetoacetate, when heated alone (uncatalyzed) with benzyl alcohol, forms synthetically useful benzyl acetoacetate (benzyl groups being easily removed later by catalytic hydrogenolysis over Pd/C under neutral conditions), via a mechanism involving acetylketene. Ethyl (and other) acetoacetates nitrosate readily with equimolar sodium nitrite in acetic acid, to afford the corresponding oximinoacetoacetate esters. A dissolving-zinc reduction of these in acetic acid in the presence of ketoesters or beta-diketones constitute the Knorr synthesis of pyrroles, useful for porphyrin synthesis. Ethyl