Réaction #65975

Équation de réaction

4-hydroxybenzaldehyde

ethanol

ethanol

sodium

HCl

ethanol

2-chloromethylquinoline

→

title compound

(2-quinolinyl)-methoxyl-benzaldehyde

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source