Hydroquinone → 4-(3-Chloro-5-nitro-phenoxy)-phenol

HRID 2197946

Reaktionsgleichung

Reaktionsgleichung von HRID 2197946
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1)[OH:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:15][C:14]1[CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzene

Produkt 1

HCID 684558224-(3-Chloro-5-nitro-phenoxy)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product from Example 193a (1.00 g, 5.0 mmol), hydroquinone (0.50 g, 4.5 mmol) and K2CO3 (0.78 g, 5.6 mmol) in DMF (10 ml) was heated at 110° C. for 3.5 hours. The reaction mixture was cooled to room temperature, diluted with H2O and then extracted with EtOAc. The extract was washed with H2O and brine, dried over MgSO4, filtered and concentrated under vacuum giving the title compound. The residue was treated with i-Pr2O and insoluble material was filtered off. The filtrate was evaporated and purified by silica gel column chromatography eluting with 5:2 EtOAc/hexane to give the title product as pale yellow oil (0.51 g, 43%).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-78700faa776a4ccd9963177adab44651
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338605B2

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