Hydrochloric Acid → 6-Nitro-2-toluonitrile

HRID 49680

Reaktionsgleichung

Reaktionsgleichung von HRID 49680
[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% pure) and 7.7 g (50 mmol) of 3-nitro-o-xylene (97% pure) 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 dropwise 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 into ice-water, the pH is adjusted to 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 toluene as mobile phase. M.p.: 101-103° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ebe185d583fa4cf3aed558a61bc0bef7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706886B2

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