p-Toluenesulfonic acid → 7-nitro-1H-indene

HRID 1434557Notes

Reaction equation

HRID 1434557 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2O)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]=[CH:8]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131024564-Nitro-2,3-dihydro-1H-inden-1-OL

Product 1

HCID 132395877-nitro-1H-indeneYield 83.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-nitroindan-1-ol (0.385 g, 2.15 mmol) and p-toluenesulfonic acid (5.0 mg, 0.03 mmol) in toluene (30 ml) was stirred and heated to reflux for 16 hours. After cooled to ambient temperature, the mixture was washed with aqueous sodium bicarbonate solution. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by preparatory TLC (hexane:ethylacetate 3:1) to afford 7-nitro-1H-indene (0.289 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. washthe mixture was washed with aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by preparatory TLC (hexane:ethylacetate 3:1)

Sources & evidence

ORD record
ord-d68f551505cb40169d3ecfbf18e456db
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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