Nitric Acid → 4-Bromo-5-nitroveratrole

HRID 1196959

Reaktionsgleichung

Reaktionsgleichung von HRID 1196959
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Produkt 1

HCID 1709684-Bromo-5-nitroveratrole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-Bromoveratrole (50 g, 0.23 mol) was added dropwise at 6°-9° to a stirred solution of 175 ml of concentrated nitric acid and glacial acetic acid (525 ml). After stirring at 6°-11° for 1.5 hours, the mixture was poured into 2.5 liters of ice-water. The light yellow solid was filtered after 0.5 hour, washed with water, and air-dried (62.5 g); m.p. 120°-122° (s. 118°). Following crystallization from 400 ml of ethanol, the title A compound as a light yellow product weighed 50.0 g; m.p. 121°-123°. Lit. m.p. 120°-122°, 122°-124° (J. Org. Chem., 25, 724 (1960).

Aufarbeitung

  1. filtrationThe light yellow solid was filtered after 0.5 hour
  2. washwashed with water
  3. customair-dried (62.5 g)
  4. customm.p. 120°-122° (s. 118°)
  5. customcrystallization from 400 ml of ethanol
  6. customLit. m.p. 120°-122°, 122°-124°

Quellen und Nachweise

ORD-Eintrag
ord-3d31bb2cb63a4cf9b1f1cc38a3a4d78a
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116851

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