Methanol → Methyl 3-(2-formylphenyl)propionate

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH2:4][CH2:5][C:6]2[C:11](C=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(=O)(O)[O-:14].[Na+].[CH3:18][OH:19]>ClCCl>[CH:18]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:14])=[O:19]

Komponenten

Versuchsvorschrift

A suspension of 4.5 g of 3-methoxy-1,2-dihydronaphthalene, 1 g of sodium bicarbonate, 20 mL of methanol and 80 mL of dichloromethane was stirred and cooled in a dry ice-acetone bath. A rapid stream of ozone was bubbled into the suspension until a persistent blue coloration was visible. The mixture was flushed with nitrogen and 3.5 mL of methyl sulfide was added. The mixture was stirred in an ice-acetone bath for 1 hour and then 2 hours at room temperature. The organic solution was washed with water, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether to provide 5.0 g (90%) of the desired title intermediate. NMR.