2-Heptanol, 6-methyl- → 6-Methyl-2-heptanone

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Reaction Steps

A mixture of 1.27 g (9.76 mmoles) of 6-methyl-2-heptanol (purchased from Aldrich Chemical Co., Milwaukee, Wis.) and 9.26 g (42.9 mmoles) of pyridinium chlorochromate (purchased from Aldrich Chemical Co., Milwaukee, Wis.) in 35 mL of dichloromethane was stirred at room temperature for 3.5 hours. At that point, the mixture was diluted with 150 mL of ether and 200 mL of 1M aqueous sodium hydroxide. After separating the layers, the organic layer was washed in successive order with 9:1 (volume/volume) 1M aqueous sodium hydroxide: saturated brine (2×100 mL), 10% aqueous sodium chloride (1×100 mL), 3:1 (volume/volume) 2M aqueous hydrochloric acid: saturated brine (3×100 mL), saturated aqueous sodium bicarbonate (1×100 mL), and saturated brine (1×100 mL). The organic layer was then dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 1.214 g (97% yield) of the named ketone. The identity and purity of this known compound were ascertained by IR and proton NMR analysis.

Provenance & Evidence