반응 #65975

반응 방정식

4-hydroxybenzaldehyde

ethanol

ethanol

sodium

HCl

ethanol

2-chloromethylquinoline

→

title compound

(2-quinolinyl)-methoxyl-benzaldehyde

반응 조건

후처리

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

실험 절차

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.

출처