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

HRID 2085851Notes

Reaction equation

HRID 2085851 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 −5iC (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, 18 M 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).

Workup

  1. additionice was added
  2. extractionthe resulting mixture was extracted with EtOAc
  3. concentrationThe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c9753ea85644760a4c246f2b5aa5e04
Source dataset
uspto-grants-2004_04
Patent number
US06720425B2

Reaction notes

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