Dichloromethane → Phenol, 2-chloro-3-nitro-

HRID 36865

Reaktionsgleichung

Reaktionsgleichung von HRID 36865
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:11]([O-])(=O)=O.[K+].ClCCl>Cl.O>[Cl:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:10]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 111373-NitrophenolHCID 6426889Potassium Chlorate

Produkt 1

HCID 3013917Phenol, 2-chloro-3-nitro-Ausbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

73 g (0.52 mol) of 3-nitrophenol are dissolved in 2 liters-of 6N hydrochloric acid while heating. The mixture is cooled in an ice bath to 28°-30° C. 32 g (0.26 mol) of potassium chlorate in 500 ml of water are added over 1.5 hours and then, at the end of the addition, the mixture is left stirring for 30 minutes at 28°-30° C. The mixture is cooled to 15° C. and 1 liter of dichloromethane is added. The layers are separated and the organic phase is washed with water. The organic phase is dried and evaporated. The residue is purified by chromatography on a column of silica gel, eluting with a dichloromethane/methanol (80/20) mixture. Recrystallization is carried out from toluene. 29 g of product are obtained.

Aufarbeitung

  1. temperaturewhile heating
  2. temperatureThe mixture is cooled in an ice bath to 28°-30° C
  3. additionat the end of the addition
  4. waitthe mixture is left
  5. customThe layers are separated
  6. washthe organic phase is washed with water
  7. customThe organic phase is dried
  8. customevaporated
  9. customThe residue is purified by chromatography on a column of silica gel
  10. washeluting with a dichloromethane/methanol (80/20) mixture
  11. customRecrystallization

Quellen und Nachweise

ORD-Eintrag
ord-945c0e5684024f81beb47d87c2e71169
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418241

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