- Synthesis of 2-Chlorocyclohexanone
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2-Chloro (CAS no.: ), which is known as Cyclohexanone, 2-chloro-, could be produced through the following synthetic route.
In a 3-l. three-necked round-bottomed flask, fitted with a gas inlet tube reaching almost to the bottom, a sealed mechanical stirrer, and a gas outlet tube connected to a mercury valve, are placed 294 g. (3 moles) of cyclohexanone (CAS no ) and 900 ml. of water. After the reaction vessel has been swept out with chlorine, the gas outlet tube is connected to the mercury valve, the flask is cooled in an ice bath, the stirrer is started, and 215 g. (slightly more than 3 moles) of chlorine is bubbled in as rapidly as the gas is absorbed (about 45 minutes).
The heavier chlorocyclohexanone layer is separated and combined with three 150-ml. ether extracts of the aqueous phase, and washed with 150 ml. of water and then with 200 ml. of saturated sodium chloride solution. After filtration (gravity) through anhydrous sodium sulfate the ether is removed and the residue vacuum-distilled in a modified Claisen flask. The fraction (300–340 g.) boiling below 100° at 10 mm. is collected. This material is then fractionated carefully under reduced pressure by means of a 42-in. modified Vigreux column (heated) with a total-condensation variable take-off head. The yield of 2-chlorocyclohexanone boiling at 90–91°/14–15 mm. is 240–265 g. (61–66%).
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