Water → 2-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene

HRID 731969

Reaktionsgleichung

Reaktionsgleichung von HRID 731969
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21]Cl.[CH3:23][C:24]1([CH3:34])[O:28][C:27]2[CH:29]=[CH:30][CH:31]=[C:32](O)[C:26]=2[O:25]1.C(=O)([O-])[O-:36].[K+].[K+].O>CN(C=O)C>[CH3:23][C:24]1([CH3:34])[O:28][C:27]2[CH:29]=[CH:30][C:31]([O:36][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:3]3[C:4]([Cl:16])=[CH:5][C:6]([O:8][CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[CH:7][C:2]=3[Cl:1])=[CH:32][C:26]=2[O:25]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62765Bendiocarb phenolHCID 222571231,3-Dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzene

Produkt 1

HCID 689998862-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzeneAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 0.3 gram (0.00083 mole) of 1,3-dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzene, 0.17 gram (0.00100 mole) of 2,2-dimethylbenzo[d]1,3-dioxolan-4-ol, and 0.17 gram (0.00125 mole) of potassium carbonate in 10 mL of DMF was heated at 80° C. for about 18 hours. After this time, the reaction mixture was cooled and 30 mL of water was added. The mixture was then extracted with three 20 mL portions of diethyl ether. The combined extracts were washed with 20 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:1 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.29 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureAfter this time, the reaction mixture was cooled
  2. extractionThe mixture was then extracted with three 20 mL portions of diethyl ether
  3. washThe combined extracts were washed with 20 mL of an aqueous solution saturated with sodium chloride
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue was purified with column chromatography on silica gel using 1:1 methylene chloride
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59a35a2f9bb440a88ac7a187a0b59c5c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585891B2

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