4-Hydroxybenzaldehyde → 4-(2-Phenoxyethoxy)benzaldehyde

Reaktionsgleichung

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[O:12]([CH2:19][CH2:20]CS([O-])(=O)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[O:12]([CH2:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

Versuchsvorschrift

1.19 g of 4-hydroxybenzaldehyde were dissolved in 30 ml of DMF, and 0.41 g of 60% NaH were further added to the resultant solution while cooling it with ice. The solution was then stirred for 1 hour after elevating the temperature of the solution up to room temperature. The solution was again cooled with ice, then added with 2.0 g of 2-phenoxyethyl-methane sulfonate, and stirred for 1 hour at room temperature and subsequently for a night at 50-60° C. The solution reacted was poured into ice-water and extracted with ethyl acetate, then the organic layer resulted was dried with anhydrous magnesium sulfate. The solvent used was then removed by distillation under reduced pressure, and the residue obtained was washed with a mixture of ether and hexane, thereby affording 1.45 g of 4-(2-phenoxyethyloxy)benzaldehyde.