Reacción #65975

Ecuación de reacción

4-hydroxybenzaldehyde

ethanol

ethanol

sodium

HCl

ethanol

2-chloromethylquinoline

→

title compound

(2-quinolinyl)-methoxyl-benzaldehyde

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is gently refluxed for 1 hour
2. 2
   TemperaturaThe mixture is refluxed for 24 hours
3. 3
   Otrothe solvent is evaporated
4. 4
   Otrothe residue is partitioned between water and ethyl acetate
5. 5
   LavadoThe organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and
6. 6
   Secadodried (MgSO4)
7. 7
   OtroRemoval of the solvent

Procedimiento

To a solution of sodium metal (0.9 g, 39.13 g.a.) in absolute ethanol (50 mL) is added dropwise under nitrogen a solution of 4-hydroxybenzaldehyde (5 g, 40.94 mmole) in absolute ethanol (50 mL). The mixture is gently refluxed for 1 hour and then treated dropwise with a solution of 2-chloromethylquinoline (free base, 7.24 g, 40.76 mmole), freshly prepared from the HCl salt) in ethanol (50 mL). The mixture is refluxed for 24 hours, the solvent is evaporated and the residue is partitioned between water and ethyl acetate. The organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and dried (MgSO4). Removal of the solvent yields the title compound as a yellow solid (9.81 g). The crude material is further purified by flash chromatography (on silica Merck-60, hexane-ethyl acetate 9:1 to remove less polar impurities and 8:2 to elute the product). Yield: 7.37 g (71.5%), m.p. 82°-83° C.

Fuente