4-Phenoxyphenol → 2-chloro-4-phenoxyPhenol

HRID 479642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479642
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])(=O)=O>C(NCC(C)C)C(C)C.C1(C)C=CC=CC=1>[Cl:18][C:10]1[CH:9]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[OH:14]

Komponenten

5

Edukt 2

HCID 132544-PhenoxyphenolHCID 24648Sulfuryl chloride

Produkt 1

HCID 107276802-chloro-4-phenoxyPhenolAusbeute 121,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8085DiisobutylamineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 54 ml toluene solution of 4-phenoxyphenol (2 g, 10.7 mmol) and diisobutylamine (0.15 ml, 0.86 mmol) was added sulfuryl chloride (0.69 ml, 8.6 mmol). The mixture was heated to 70° C. for 3 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and aq sat. bicarbonate solution. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 15% AcOEt/hexanes gave the title compound 2.3 g as colorless syrup (97%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and aq sat. bicarbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washElution with 15% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f97b5c33e0e2442bb3049c1ed99ad030
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645997B2

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