反応 #535341

反応方程式

H2O

1-methylnaphthalene

nitric acid

nitric acid

→

1

収率 43.0%

8-amino-2-naphthol

収率 43.0%

反応条件

後処理

1. 1
   抽出The aqueous solution was extracted with benzene twice
2. 2
   洗浄the combined benzene solution was washed with 10% NaOH solution
3. 3
   乾燥dried with Na2SO4
4. 4
   濃縮concentrated
5. 5
   その他Silica gel chromatography (EtOAc:Hexanes=5:95) gave product
6. 6
   workup.ADDITIONstill containing a few percentage of the other regioisomer
7. 7
   その他It was recrystallized with EtOAc/Hexanes

実験手順

To 1-methylnaphthalene (8.0 g, 56 mmol) in round bottom flask at 0° C. was added nitric acid (26 mL) dropwise. (NOTE: A slow addition of nitric acid is most important to avoid the formation of the other regioisomers). After the reaction mixture was stirred for an additional 15 min at 0° C., it was poured into 65 mL of H2O. The aqueous solution was extracted with benzene twice and the combined benzene solution was washed with 10% NaOH solution, dried with Na2SO4, and concentrated. Silica gel chromatography (EtOAc:Hexanes=5:95) gave product still containing a few percentage of the other regioisomer. It was recrystallized with EtOAc/Hexanes to give 9.0 g (43%) of 1.

出典