Acetic Acid → 4-Nitroindan-1-one

HRID 2377228Notes

Reaction equation

HRID 2377228 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2)([O-:3])=[O:2].C(O)(=[O:15])C>[O-2].[Cr+6].[O-2].[O-2]>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 176Acetic Acid3×HCID 2535784-Nitroindan

Product 1

HCID 905634-Nitroindan-1-one

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst2×

Procedure

A suspension of chromium(VI) oxide (36.7 g, 367.7 mmol) in acetic acid (400 mL) was added slowly to a solution of 4-nitroindane (20 g, 122.6 mmol) in glacial acetic acid (500 mL). Extra acetic acid (200 mL) was used to transfer all the chromium(VI)oxide. The reaction was stirred vigorously at room temperature for about 5 hours and was then quenched with water (200 mL). Most of the acetic acid was removed under high vacuum and the crude product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using first hexane/ethyl acetate (20:1) as eluent to remove unreacted starting material and then hexane/ethyl acetate (10:1) to provide the desired product. MS (ESI): m/z 176 (M−H)−.

Workup

  1. customwas then quenched with water (200 mL)
  2. customMost of the acetic acid was removed under high vacuum
  3. extractionthe crude product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel using first hexane/ethyl acetate (20:1) as eluent
  9. customto remove unreacted

Sources & evidence

ORD record
ord-b85665eeeceb4d54ae3f91b18b13ff4e
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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