反応 #65975

反応方程式

4-hydroxybenzaldehyde

ethanol

ethanol

sodium

HCl

ethanol

2-chloromethylquinoline

→

title compound

(2-quinolinyl)-methoxyl-benzaldehyde

反応条件

後処理

1. 1
   温度The mixture is gently refluxed for 1 hour
2. 2
   温度The mixture is refluxed for 24 hours
3. 3
   その他the solvent is evaporated
4. 4
   その他the residue is partitioned between water and ethyl acetate
5. 5
   洗浄The organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and
6. 6
   乾燥dried (MgSO4)
7. 7
   その他Removal of the solvent

実験手順

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.

出典