Reacción #66786

Ecuación de reacción

1,2-dichloro-4-nitrobenzene

pyridin-2-ylmethanol

potassium hydroxide

water

→

title compound

Rendimiento 48.3%

2-[(2-Chloro-4-nitrophenoxy)methyl]pyridine

Rendimiento 48.3%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe layers were separated
2. 2
   workup.ADDITIONthe organic layer was diluted with ethyl acetate
3. 3
   Lavadowashed with water
4. 4
   SecadoThe organic layer was dried over sodium sulfate
5. 5
   Otrothe solvent was removed in vacuo
6. 6
   OtroThe residue was triturated with petroleum ether and tert-butyl methyl ether

Procedimiento

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.

Fuente