تفاعل #583128

معادلة التفاعل

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

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر