Diisobutylamine → 2-Chloro-4-(oxan-4-yl)phenol

HRID 991588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991588
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(NCC(C)C)C(C)C.S(Cl)([Cl:26])(=O)=O>C1(C)C=CC=CC=1>[Cl:26][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][C:10]=1[OH:13]

Komponenten

5

Edukt 3

HCID 8085DiisobutylamineHCID 24648Sulfuryl chloride2×HCID 227373584-(Oxan-4-yl)phenol

Produkt 1

HCID 184146372-Chloro-4-(oxan-4-yl)phenolAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 30 ml Toluene solution of 4-(4-tetrahydropyranyl)phenol 1 g (5.61 mmol) and diisobutylamine 0.08 ml (0.46 mmol) was added sulfuryl chloride 0.51 ml (6.35 mmol) over 3 hr period upon heating at 70° C. Stirring was continued at that temp. for 2 hr after the addition of sulfuryl chloride was complete. The solvent was removed under reduced pressure, diluted with ethyl acetate and washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes: ethyl acetate) to give 0.941 g of the title compound as while solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (hexanes: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-76698d8fdca94847baf91ee1b2cf2f62
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465497B2

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