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5.ii ii)
ii) Production of 4-chloro-6-methyl-2-pyridinecarboxyaldehyde 1.38 g (8.8 mmol) of 4-chloro-6-methyl-2-pyridinylmethanol was dissolved in 20 ml of benzene. The resultant solution was added with 3.3 g of activated manganese dioxide (manufactured by Aldrich), and the mixture was heated so as to elevate the temperature of the mixture to the reflux temperature. After the mixture has reached the reflux temperature, it was stirred continuously all night to complete a reaction. The reacted mixture was then cooled, and the temperature of the mixture was maintained at a room temperature. Then, the insoluble materials in the mixture were removed by filtration. The filtrate obtained was condensed under reduced pressure to obtain the target compound in an amount of 1.08 g. 1H-NMR (CDCl3, TMS, δ ppm) data; 2.63 (s, 3H), 7.40 (d, 1H), 7.78 (d, 1H), 10.00 (s, 1H).
With manganese(IV) oxide In benzene for 3h; Heating / reflux;
8.ii
14.0 g (88.8 mmol) of 4-chloro-6-methyl-2-pyridinylmethanol was dissolved in 100 ml of benzene, and 28.0 g of activated manganese dioxide was added. The resulting solution was refluxed for 3 hours. The reaction solution was cooled. The insoluble matter was separated by filtration through celite. The filtrate was concentrated under reduced pressure to give 6.1 g of the target compound.
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