Hydrochloric Acid → 6-Nitro-2-toluonitrile

HRID 397155

Reaktionsgleichung

Reaktionsgleichung von HRID 397155
[N:1](OCCCC)=O.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[CH3:18])([O-:10])=[O:9].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[C:12]=1[C:18]#[N:1]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 10996Butyl nitriteHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 746696-Nitro-2-toluonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 16 g (150 mmol) of n-butyl nitrite (97%) and 7.7 g (50 mmol) of 3-nitro-o-xylene (97%) in 50 ml of dimethylformamide is cooled to from −5 to −10° C., and a solution of 11 g (100 mmol) of potassium tert-butoxide in 50 ml of dimethylformamide is added at this temperature, over a period of 1.5 hours. The reaction mixture is stirred at room temperature for another 6 days. For work-up, the mixture is poured onto ice-water and adjusted to pH 1 using hydrochloric acid, and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate and concentrated. This gives 8.2 g of product. The 2-methyl-6-nitrobenzonitrile can be purified by silica gel chromatography using the mobile phase toluene. M.p.: 101-103° C.

Aufarbeitung

  1. additionFor work-up, the mixture is poured onto ice-water
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe 2-methyl-6-nitrobenzonitrile can be purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c5a458fa710449e4a62f83bfa96e7511
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608209B2

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