Nitric Acid → HCID 67815034, compound

HRID 1756775Notes

Reaction equation

HRID 1756775 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[O:20][CH3:21])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH3:2].[N+:23]([O-])([OH:25])=[O:24]>O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([C:12]1[CH:17]=[C:16]([N+:23]([O-:25])=[O:24])[CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[O:20][CH3:21])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 54099120HCID 54099120, compound

Product 1

HCID 67815034HCID 67815034, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.13 g (3.66 mmol) of 3-(2, 3-dimethoxyphenyl) octanoic acid ethyl ester and 3 ml of 60% nitric acid was stirred at room temperature for 2 hours. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/5) to give 1.15 g of 3-(2, 3-dimethoxy-5-nitropheyl) octanoic acid ethyl ester as a yellow oil. Yield, 89%. This compound showed a coupling constant of J=2.6 Hz in 1H NMR (CDCl3) spectra, suggesting meta-coupling. Further, 0.10 g of 3-(2, 3-dimethoxy-6-nitrophenyl) octanoic acid etheyl ester (yield, 7.7%) was obtained, showing a coupling constant of J=9.1 Hz in 1H NMR (CDCl3) spectra.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with ethyl acetate/hexane (1/5)

Sources & evidence

ORD record
ord-ff904decd24c419ebf8eb204447adb1d
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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