Diethyl Ether → 3-Fluoro-p-anisaldehyde

To a solution of o-fluoroanisole, 101 g (0.80 mol) in 50 ml dry methylene chloride is added dropwise over 30 minute a solution of titanium tetrachloride, 182 g (0.96 mol, 1.2 equiv.) and α,α-dichloromethylmethyl ether, 110 g (0.96 mol) in an equal volume of methylene chloride. The temperature is maintained at 10°-20° C. with an ice-bath. The mixture is stirred at room temperature for one hour longer, and then poured over crushed ice-water with stirring. Ether (1 l) is added, and the mixture is stirred under nitrogen until solution occurs. The organic layer is extracted with water, sodium bicarbonate solution and is dried (MgSO4). The solvent is evaporated at 30° to leave crude product as an oil. When vacuum distilled through a jacketed Vigreux column, the oil gives 3-fluoro-4-methoxybenzaldehyde, B.P. 120°-12120 C. at 10 mm. Hg; Rf 0.6 on a silica-gel G plate with methylene chloride.

1. temperatureThe temperature is maintained at 10°-20° C. with an ice-bath
2. additionpoured
3. stirringwith stirring
4. stirringthe mixture is stirred under nitrogen until solution
5. extractionThe organic layer is extracted with water, sodium bicarbonate solution
6. dry with materialis dried (MgSO4)
7. customThe solvent is evaporated at 30°
8. customto leave crude product as an oil
9. distillationWhen vacuum distilled through a jacketed Vigreux column

ORD record

ord-1aedde8ac68049518fab446edfa43f50

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05696159