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The product is isolated from the mixture by the following work-up: [3] Synthesis of 4-methylcyclohexene with work-up step in red. A concentrated solution of sodium chloride in water, known as a brine solution, is added to the mixture and the layers are allowed to separate. The brine is used to remove any acid or water from the organic layer.
Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. [1] It is typically performed during the work-up step following a chemical synthesis to purify crude compounds [2] and results in the product being largely free of acidic or basic impurities.
The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which facilitates workup. Solutions of DDQ in benzene are red, due to the formation of a charge-transfer complex. [9]
The mechanism of the reaction involves two steps. The first step is a nucleophilic addition to the nitrile with the aid of a polarizing Lewis acid, forming an imine, which is later hydrolyzed during the aqueous workup to yield the final aryl ketone. Hoesch reaction mechanism
In the cited example the Lewis acid TiCl 4 is used. First, the Lewis acid activates the aldehyde component followed by carbon-carbon bond formation between the enol silane and the activated aldehyde. With the loss of a chlorosilane the compound 1 is built. The desired product, a racemate of 2 and 3, is obtained by aqueous work-up. [3]
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For example, nonylmagnesium bromide reacts with methyl p-chlorobenzoate to give p-nonylbenzoic acid, in the presence of Tris(acetylacetonato)iron(III) (Fe(acac) 3), after workup with NaOH to hydrolyze the ester, shown as follows. Without the Fe(acac) 3, the Grignard reagent would attack the ester group over the aryl halide. [21]
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