Hydrochloric Acid → 1-(5-Chloro-2-thienyl)cyclohexanol

HRID 1534993

Reaktionsgleichung

Reaktionsgleichung von HRID 1534993
[Mg].[Cl:2][C:3]1[S:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>C1COCC1.C1C=CC=CC=1.O>[Cl:2][C:3]1[S:4][C:5]([C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 185012,5-DichlorothiopheneHCID 5462224Magnesium

Produkt 1

HCID 199088921-(5-Chloro-2-thienyl)cyclohexanolAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a Grignard reagent prepared from magnesium (26.7 g), 2,5-dichlorothiophene (16.83 g) and anhydrous THF (70 ml) was added dropwise in small portions a solution of cyclohexanone (XIa) (9.815 g) in anhydrous THF (30 ml) with stirring under ice-cooling in nitrogen atmosphere. The mixture was made to react at room temperature for 3 hours and after addition of water and acidification with 5% hydrochloric acid, extracted with chloroform. The extract was washed with water, dried and evaporated. The residue was applied to column chromatography on silica gel (70 g). From the benzene fraction, 1-(5-chloro-2-thienyl)cyclohexanol (Xa) (17.6 g) was obtained as an oil (yield 81.2%).

Aufarbeitung

  1. temperaturecooling in nitrogen atmosphere
  2. customto react at room temperature for 3 hours
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0737d4c3d14f464e80a8ef4630454707
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091539

Verknüpfte Notizen

Wird geladen…