Reaktion #684961

Reaktionsgleichung

acetic acid

sodium hydroxide

m-anisaldehyde

nitromethane

→

title compound

Ausbeute 83.5%

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

Ausbeute 83.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehigher than 30° C
2. 2
   TemperaturUpon cooling on ice
3. 3
   Sonstigethe resulting reaction mixture
4. 4
   Extraktionwas extracted with ethyl acetate
5. 5
   WaschenThe ethyl acetate layer was washed successively with water
6. 6
   Trocknena 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

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).

Quelle