Pyridine → HCID 54312588, Verbindung

HRID 1939662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1939662
O[C:2]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[Cl:13])([CH3:5])[CH:3]=[CH2:4].N1C=CC=CC=1.S(Cl)([Cl:22])=O>C(Cl)Cl>[Cl:22][CH2:4][CH:3]=[C:2]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[Cl:13])[CH3:5]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 214679933-Hydroxy-3-(2,5-dichlorophenyl)-1-butene

Produkt 1

HCID 54312588HCID 54312588, VerbindungAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, a stirred solution of 12.0 grams (0.056 mole) of 3-hydroxy-3-(2,5-dichlorophenyl)-1-butene and 4.7 grams (0.056 mole) of pyridine in 85 mL of methylene chloride is cooled in an ice-water bath, and 6.6 grams (0.056 mole) of thionyl chloride is added dropwise. Upon completion of addition, the reaction mixture is stirred for about one hour. After this time the reaction mixture is diluted with 50 mL of methylene chloride and about 50 grams of ice. The mixture is stirred until the ice melts, and then the organic layer is separated. The organic layer is washed in turn with two 50 mL portions of an aqueous 0.5M solution of hydrochloric acid, two 50 mL portions of an aqueous solution saturated with sodium bicarbonate, two 50 mL portions of water, and two 50 mL portions of an aqueous solution saturated with sodium chloride. The organic layer is then dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 5.5 grams of 1-chloro-3-(2,5-dichlorophenyl)-2-butene. The NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. additionUpon completion of addition
  2. customthe organic layer is separated
  3. washThe organic layer is washed in turn with two 50 mL portions of an aqueous 0.5M solution of hydrochloric acid, two 50 mL portions of an aqueous solution saturated with sodium bicarbonate, two 50 mL portions of water, and two 50 mL portions of an aqueous solution saturated with sodium chloride
  4. dry with materialThe organic layer is then dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3008edd8e0b04d61aee9a377fd760a75
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696259

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