반응 #583128

반응 방정식

H2SO4

HNO3

H2SO4

3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone

→

title compound

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

반응 조건

후처리

1. 1
   기타at −5° C.
2. 2
   workup.ADDITIONice was added
3. 3
   추출the resulting mixture extracted with EtOAc
4. 4
   농축The combined extracts were concentrated under reduced pressure

실험 절차

To 1.7 ml (3.0 g, 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-1(2H)-naphthalenone. A solution of 426.7 mg (6.88 mmol, 0.43 ml, 16M) HNO3, and 1.31 g (0.013 mol, 0.74 ml, 18 M) H2SO4 was slowly added. After 20 minutes, ice was added and the resulting mixture extracted with EtOAc. The combined extracts were concentrated under reduced pressure to give a residue from which the title compound, a pale yellow solid, was isolated by column chromatography (10% EtOAC/hexanes). 1H NMR (CDCl3): δ 8.83 (1H, d, J=2.6 Hz), 8.31 (1H, dd, J=2.8, 8.9 Hz), 7.62 (1H, d, J=8.7 Hz), 2.81 (2H, t, J=6.5 Hz), 2.08 (2H, t, J=6.5 Hz), 1.45 (6H, s).

출처