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

HRID 1955558Notes

Reaction equation

HRID 1955558 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, 18M) 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-7cc5ff8f3e50446c8d6ee937ace72d1b
Source dataset
uspto-grants-1998_07
Patent number
US05776699

Reaction notes

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