Реакция #684961

Уравнение реакции

acetic acid

sodium hydroxide

m-anisaldehyde

nitromethane

→

title compound

Выход 83.5%

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

Выход 83.5%

Растворители

methanol

Условия реакции

Обработка

1. 1
   Другоеhigher than 30° C
2. 2
   ТемператураUpon cooling on ice
3. 3
   Другоеthe resulting reaction mixture
4. 4
   Экстракцияwas extracted with ethyl acetate
5. 5
   ПромывкаThe ethyl acetate layer was washed successively with water
6. 6
   Сушкаa 5% aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ДругоеThe residue was purified by silica gel column chromatography

Методика

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).

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