Potassium Carbonate → Tert-butyl 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetate

HRID 908655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908655
[Cl:1][C:2]([Cl:15])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]([Cl:14])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C.O>[Cl:15][C:2]([Cl:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Cl:14])[C:9]([O:13][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:10]([Cl:12])[CH:11]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Produkt 1

HCID 59366522Tert-butyl 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetateAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 0.5 gram (0.0017 mole) of 4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenol (known compound), 0.26 gram (0.0019 mole) of potassium carbonate and 0.26 gram (0.0017 mole) of tert-butyl chloroacetate in 0.12 mL of DMF was heated to 70° C. where it stirred for about 18 hours. After this time the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with 30 mL of water then extracted with three 30 mL portions of ethyl acetate. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a yellow oil. The crude oil was purified with column chromatography on silica gel using a mixture of hexanes and ethyl acetate (93:7) as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.7 gram of the subject compound.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. extractionthen extracted with three 30 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a yellow oil
  6. customThe crude oil was purified with column chromatography on silica gel using
  7. additiona mixture of hexanes and ethyl acetate (93:7) as an eluant
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2707f5d9892d4c47828c816ebcb3fbc2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017635B2

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