Nitric Acid → 4,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 495946Notes

Reaction equation

HRID 495946 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[CH2:9][CH2:8]1.[N+:19]([O-])([OH:21])=[O:20]>>[CH3:6][C:7]1([CH3:18])[C:16]2[C:11](=[CH:12][C:13]([N+:19]([O-:21])=[O:20])=[CH:14][CH:15]=2)[C:10](=[O:17])[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 134632924,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one

Procedure

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).

Workup

  1. customat −5° C.
  2. additionice was added
  3. extractionthe resulting mixture extracted with EtOAc
  4. concentrationThe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-eeae68cc47684094a6bafc9410ab3241
Source dataset
uspto-grants-2005_09
Patent number
US06942980B1

Reaction notes

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