تفاعل #65975

معادلة التفاعل

4-hydroxybenzaldehyde

ethanol

ethanol

sodium

HCl

ethanol

2-chloromethylquinoline

→

title compound

(2-quinolinyl)-methoxyl-benzaldehyde

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is gently refluxed for 1 hour
2. 2
   درجة الحرارةThe mixture is refluxed for 24 hours
3. 3
   أخرىthe solvent is evaporated
4. 4
   أخرىthe residue is partitioned between water and ethyl acetate
5. 5
   غسيلThe organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and
6. 6
   تجفيفdried (MgSO4)
7. 7
   أخرىRemoval of the solvent

الإجراء التجريبي

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.

المصدر