- A General Synthetic Method for the Preparation of 2-Decanone
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This synthetic process of 2-Decanone (CAS NO. ) occurs in a flask. A 100 mL, three-necked, round-bottomed flask is fitted with a magnetic stirrer and a pressure-equalizing dropping funnel containing 1-decene (4.2 g, 30 mmol). The flask is charged with a mixture of palladium chloride (0.53 g, 3 mmol), cuprous chloride (2.97 g, 30 mmol), and aqueous dimethylformamide (DMF/H2O = 7:1, 24 mL). With the other outlets securely stoppered and wired down, an oxygen-filled balloon is placed over one neck, and the flask is stirred at room temperature to allow oxygen uptake. After 1 hr, 1-decene (4.2 g, 30 mmol) is added over 10 min using the dropping funnel, and the solution is stirred vigorously at room temperature under an oxygen balloon. The color of the solution turns from green to black within 15 min and returns gradually to green. After 24 hr, the mixture is poured into cold 3 N hydrochloric acid (100 mL) and extracted with five 50 mL portions of ether. The extracts are combined and washed successively with 50 mL of saturated sodium bicarbonate solution, 50 mL of brine, and then dried over anhydrous magnesium sulfate. After filtration, the solvent is removed by evaporation and the residue is distilled using a 15-cm Vigreux column to give 2-decanone as a colorless oil (3.0–3.4 g, 65–73%, bp 43–50°C/1 mm).
The synthetic route is as follows:
2-Decanone belongs to methyl ketones. Methyl ketones are important intermediates for the synthesis of methyl alkyl carbinols, annulation reagents, and cyclic compounds. Compared with other synthetic methods, the palladium-catalyzed oxidation of 1-olefins described here is more convenient and practical. The industrial method of ethylene oxidation to using PdCl2–CuCl2–O2 is the original reaction of this type. The oxidation of various olefins has been carried out.
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