Water → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

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To a mixture of pyridin-2-ylmethanol (6.82 g, 62.5 mmol), Aliquat 336 (8.08 g, 20.0 mmol), potassium hydroxide (3.51 g, 62.5 mmol) and water (40 mL) were added toluene (80 mL) and 1,2-dichloro-4-nitrobenzene (10.0 g, 52.1 mmol). The mixture was heated to 60° C. overnight with vigorous stirring. The layers were separated, and the organic layer was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with petroleum ether and tert-butyl methyl ether to yield 6.66 g (48%) of the title compound.

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