p-Toluenesulfonic acid → 4-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester

HRID 386337

Reaktionsgleichung

Reaktionsgleichung von HRID 386337
[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][C:15]([CH3:19])([CH3:18])[CH2:16]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][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 1425013-Bromo-2,2-dimethyl-1-propanolHCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acid

Produkt 1

HCID 592890294-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 3-bromo-2,2-dimethyl-propan-1-ol (10.0 g, 59.9 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 filtration through a silica pad using petrol as eluant. Evaporation of the appropriate fractions gives 4-propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester as a liquid. The structure is confirmed by 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. filtrationis achieved by filtration through a silica pad
  7. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-cd78500ab0584a6ebb5131e7949cf338
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372307B2

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