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

HRID 635601Notes

Reaction equation

HRID 635601 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 (3.0g, 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-9f79eee4e03c479a9ef8485ac84d7517
Source dataset
uspto-grants-2001_02
Patent number
US06187933B1

Reaction notes

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