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

HRID 1434557

Reaktionsgleichung

Reaktionsgleichung von HRID 1434557
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 132395877-nitro-1H-indeneAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d68f551505cb40169d3ecfbf18e456db
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615557B2

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