Nitric Acid → 4-Chloro-2-nitro-3-(trifluoromethyl)phenol

HRID 2190833

Reaktionsgleichung

Reaktionsgleichung von HRID 2190833
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].S(=O)(=O)(O)O.[N+:18]([O-:21])([OH:20])=[O:19]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([C:9]([F:10])([F:11])[F:12])=[CH:4][C:5]([OH:8])=[C:6]([N+:18]([O-:20])=[O:19])[CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:18]([O-:21])=[O:19])[C:3]=1[C:9]([F:10])([F:11])[F:12]

Komponenten

6

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 805204-Chloro-3-(trifluoromethyl)phenol

Produkt 2

HCID 581482394-Chloro-2-nitro-3-(trifluoromethyl)phenolHCID 668796884-Chloro-2-nitro-5-(trifluoromethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 5.0 g of 4-chloro-3-trifluoromethylphenol and 20 ml of acetic acid, 1.5 ml of concentrated sulfuric acid and then 2.6 g of 69% nitric acid were added dropwise while ice-cooling. To the reaction mixture, 3 ml of concentrated sulfuric acid was added dropwise at room temperature, and stirred for three hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.3 g of 4-chloro-2-nitro-5-trifluoromethylphenol, 1.57 g of 4-chloro-2-nitro-3-trifluoromethylphenol.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c02967c0b6df410481e5eb41e603ba61
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324387B2

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