p-Toluenesulfonic acid → 3-(3-Methylcyclohex-1-en-1-yl)thiophene

HRID 2295846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295846
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2(O)[CH2:11][CH2:10][CH2:9][CH:8]([CH3:12])[CH2:7]2)=[CH:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:12][CH:8]1[CH2:9][CH2:10][CH2:11][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:7]1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 132459373-Methyl-1-(thiophen-3-yl)cyclohexan-1-ol

Produkt 1

HCID 132459363-(3-Methylcyclohex-1-en-1-yl)thiopheneAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred solution of 37.6 g (0.192 mol) of 1-(3-thienyl)-3-methylcyclohexanol and 0.5 g of p-toluenesulfonic acid in 200 mL of toluene was heated under reflux, and by-product water was collected in a Dean-Stark trap attached to the reaction vessel. After about 16.5 hours, the reaction mixture was cooled and concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 11.6 g of 3-methyl-1-(3-thienyl)cyclohexene b.p. 105° C.±5° C./0.25 mm.

Aufarbeitung

  1. temperatureunder reflux
  2. customby-product water was collected in a Dean-Stark trap
  3. temperaturethe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customto give a residual oil
  6. distillationThe oil was subjected to distillation under reduced pressure
  7. distillationdistilling system

Quellen und Nachweise

ORD-Eintrag
ord-ee061c290a3f4d53b4215526328ab46a
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04426524

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