Water → 1-Cyclopropyl-1-(4-chlorophenyl)-3-chloro-1-propene

HRID 1588888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588888
[CH:1]1([C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)(O)[CH:5]=[CH2:6])[CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)([Cl:23])=O.O>C(OCC)C.CCCCCC>[CH:1]1([C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:5][CH2:6][Cl:23])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 150420331-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-ol

Produkt 1

HCID 539848831-Cyclopropyl-1-(4-chlorophenyl)-3-chloro-1-propeneAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A stirred solution of 11.0 grams (0.053 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-2-propen-1-ol and 4.6 grams (0.058 mole) of pyridine in 100 ml of diethyl ether was cooled to 0°C., and 6.8 grams (0.058 mole) of thionyl chloride was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was stirred for 30 minutes and then was taken up in 100 ml of hexane; 50 ml of water was then carefully added. The aqueous layer was separated and was extracted with hexane. The organic layers were combined and washed with 25 ml of water and then with 25 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 8.6 grams of 1-cyclopropyl-1-(4-chlorophenyl)-3-chloro-1-propene.

Aufarbeitung

  1. additionUpon completion of addition
  2. customThe aqueous layer was separated
  3. extractionwas extracted with hexane
  4. washwashed with 25 ml of water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-63b766b0660742ceabd5b1203c2c76ed
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223536

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