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Oxidation of Methylene Groups to Carbonyl Groups

Oxidation of Methylene Groups to Carbonyl Groups: Experimental Procedure

Oxidation of tetralin to 1-tetralone.


A mixture of 750 mL acetic acid, 25 g cobalt(II) acetate tetrahydrate and 30 g cobalt(II) bromide hexahydrate in a 2-L flask equipped with stirrer, thermometer and reflux condenser is vigorously stirred at 40°C. Oxygen is bubbled into the stirred mixture and a solution of 330 g tetralin and 255 g acetic acid anhydride is added dropwise within 30 min. The temperature of the reaction mixture has to be kept at 40°C. Oxygen is absorbed at a rate of 1,200 mL per min. After an additional 30 min, the reaction is quenched with ice water and the product extracted with ether. The extract is washed with a cold solution of sodium carbonate, dried over magnesium sulfate and distilled. The yield is 62%.

In general, the preparation of carbonyl compounds in the laboratory is carried out either by oxidation or dehydrogenation of primary or secondary alcohols.

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