Reacción #1479

Ecuación de reacción

H2SO4

HNO3

H2SO4

3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one

→

title compound

3,4-dihydro-4,4-dimethyl-7-nitro-naphthalen-1(2H)-one

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 5° C.
2. 2
   workup.ADDITIONice was added
3. 3
   Extracciónthe resulting mixture was extracted with EtOAc
4. 4
   ConcentraciónThe combined extracts were concentrated under reduced pressure

Procedimiento

To 1.7 mL (3.0g, 30.6 mmol, 18M) H2SO4 at 5° C. (ice-NaCl bath) was slowly added 783.0 mg (4.49 mmol) of 3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one. A solution of HNO3 (426.7 mg 6.88 mmol, 0.43 mL, 16M), and 1.31 g (0.013 mol, 0.74 mL, 18M) Of H2SO4 were slowly added. After 20 min, ice was added and the resulting mixture was extracted with EtOAc. The combined extracts were concentrated under reduced pressure to give a yellow oil from which the title compound, a pale yellow solid, was isolated by column chromatography (10% EtOAC/hexanes).

Fuente