Реакция #1479

Уравнение реакции

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

Условия реакции

Обработка

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

Методика

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).

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