2,4,6-Trichlorophenol → Methyl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate

HRID 364823

Reaktionsgleichung

Reaktionsgleichung von HRID 364823
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[K].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[C:18]=1[OH:25]>CS(C)=O.O>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([O:25][C:18]2[C:17]([Cl:16])=[CH:22][C:21]([Cl:23])=[CH:20][C:19]=2[Cl:24])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 69142,4,6-TrichlorophenolHCID 171018Methyl 5-chloro-2-nitrobenzoateHCID 5462222Potassium

Produkt 1

HCID 443063Methyl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 5-chloro-2-nitro-benzoate (17.0 g, 0.079 mole) and the potassium salt of 2,4,6-trichlorophenol (18.6 g., 0.079 mole) in dimethyl sulfoxide (100 ml.) was heated at 90° C. for 17 hours. The cooled reaction mixture was diluted with water (500 ml.) and then extracted with ether (3×100 ml.). The combined ether fractions were washed with 10% sodium hydroxide solution (2×30 ml.) and then with a saturated aqueous sodium chloride solution. The ether solution was dried (Na2SO4) and the solvent evaporated to give a dark oil. Two crystallizations (petroleum ether) gave 1.91 g. of a pale yellow solid, m.p. 101°-103° C.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with ether (3×100 ml.)
  3. washThe combined ether fractions were washed with 10% sodium hydroxide solution (2×30 ml.)
  4. dry with materialThe ether solution was dried (Na2SO4)
  5. customthe solvent evaporated
  6. customto give a dark oil
  7. customTwo crystallizations (petroleum ether)
  8. customgave 1.91 g

Quellen und Nachweise

ORD-Eintrag
ord-777ede2e74a147eea3d28e3dac95ef96
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04606758

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