p-Toluenesulfonic acid → HCID 59289068, Verbindung

HRID 386335

Reaktionsgleichung

Reaktionsgleichung von HRID 386335
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:11][C:10]([CH:7]1[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]1)=[O:12]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 1183884-BromobutanolHCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acid

Produkt 1

HCID 59289068HCID 59289068, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 4-bromobutan-1-ol (9.2 g, 60.0 mmol) and a catalytic amount of para-toluene sulphonic acid are stirred under reflux in toluene (300 ml) in a flask equipped with Dean-Stark apparatus over night. The solution is allowed to cool to room temperature, is washed with aqueous sodium carbonate and water, dried and evaporated to dryness. Purification is achieved by flash column chromatography using petrol as eluant. Evaporation of the appropriate fractions gives 4-propyl-cyclohexanecarboxylic acid 4-bromo-butyl ester as the product. The structure is confirmed by 1H NMR spectroscopy and GCMS.

Aufarbeitung

  1. customequipped with Dean-Stark apparatus over night
  2. washis washed with aqueous sodium carbonate and water
  3. customdried
  4. customevaporated to dryness
  5. customPurification
  6. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-e569159be1f043a180086ddbee91d01a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372307B2

Verknüpfte Notizen

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