Reacción #684961

Ecuación de reacción

acetic acid

sodium hydroxide

m-anisaldehyde

nitromethane

→

title compound

Rendimiento 83.5%

1-(3-Methoxyphenyl)-2-nitro-1-ethanol

Rendimiento 83.5%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrohigher than 30° C
2. 2
   TemperaturaUpon cooling on ice
3. 3
   Otrothe resulting reaction mixture
4. 4
   Extracciónwas extracted with ethyl acetate
5. 5
   LavadoThe ethyl acetate layer was washed successively with water
6. 6
   Secadoa 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

An aqueous sodium hydroxide solution (1.5 g of sodium hydroxide (37 mmol) was dissolved in 15 ml of water) was added dropwise to a solution of m-anisaldehyde (5.0 g, 37 mmol) and nitromethane (4.0 ml, 73 mmol) in methanol (50 ml) keeping the temperature of the solution at not higher than 30° C. The reaction mixture was then stirred at room temperature for 4 hours. Upon cooling on ice, an aqueous acetic acid solution (glacial acetic acid (37 mmol) was dissolved in 250 ml of water) was added, the resulting reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (6.09 g).

Fuente