Reacción #638545

Ecuación de reacción

H2O

1-methylnaphthalene

nitric acid

nitric acid

→

1

Rendimiento 43.0%

8-amino-2-naphthol

Rendimiento 43.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe aqueous solution was extracted with benzene twice
2. 2
   Lavadothe combined benzene solution was washed with 10% NaOH solution
3. 3
   Secadodried with Na2SO4
4. 4
   Concentraciónconcentrated
5. 5
   OtroSilica gel chromatography (EtOAc:Hexanes=5:95) gave product
6. 6
   workup.ADDITIONstill containing a few percentage of the other regioisomer
7. 7
   OtroIt was recrystallized with EtOAc/Hexanes

Procedimiento

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.

Fuente