Nitric Acid → 1-Chloro-5-methoxy-2-methyl-4-nitrobenzene

HRID 272680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272680
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH3:21]>O>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([N+:8]([O-:11])=[O:9])=[CH:15][C:14]=1[CH3:21]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 69517572-Chloro-4-methoxytoluene

Produkt 1

HCID 138601931-Chloro-5-methoxy-2-methyl-4-nitrobenzeneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Acetic anhydride (10 mL) at −10° C. was treated with concentrated nitric acid (>69% pure, 1 mL) and then treated portionwise with 2-chloro-4-methoxy-1-methylbenzene (0.78 g, 5 mmol) at a rate that maintained the internal temperature lower than −5° C. The solution was stirred for additional one hour while warming to room temperature, poured into an ice and water mixture, and extracted with ethyl acetate several times. The organic layers were combined, washed with 10% Na2CO3 and brine, dried (MgSO4), and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes/ethyl acetate to provide 0.75 g (71%) of the desired product. MS (DCI) m/e 219 (M+NH4)+; 1H NMR (CDCl3, 300 MHz) δ 7.78 (s, 1H), 7.09 (s, 1H), 3.94 (s, 3H), 2.35 (s, 3H).

Aufarbeitung

  1. temperaturewhile warming to room temperature
  2. extractionextracted with ethyl acetate several times
  3. washwashed with 10% Na2CO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1aa7025d750e4edb970f742dc689a65a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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