Reaction #2069954

Reaction equation

acetic acid

sodium hydroxide

m-anisaldehyde

nitromethane

→

title compound

Yield 83.5%

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

Yield 83.5%

Solvents

methanol

Conditions

Workup

1. 1
   Otherhigher than 30° C
2. 2
   TemperatureUpon cooling on ice
3. 3
   Otherthe resulting reaction mixture
4. 4
   Extractionwas extracted with ethyl acetate
5. 5
   WashThe ethyl acetate layer was washed successively with water
6. 6
   Dryinga 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   OtherThe residue was purified by silica gel column chromatography

Procedure

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).

Source