Isobutylene oxide → 2-[1-(3,3-Dimethylcyclohexyl)ethoxy]-2-methyl-1-propanol

HRID 132980

Reaktionsgleichung

Reaktionsgleichung von HRID 132980
[Cl-].[Cl-].C([Al+2])C.[CH3:6][C:7]1([CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]([CH:13]([OH:15])[CH3:14])[CH2:8]1.[CH3:17][C:18]1([O:21][CH2:20]1)[CH3:19]>C1(C)C=CC=CC=1.C1CCCCC1>[CH3:16][C:7]1([CH3:6])[CH2:12][CH2:11][CH2:10][CH:9]([CH:13]([O:15][C:18]([CH3:19])([CH3:17])[CH2:20][OH:21])[CH3:14])[CH2:8]1

Komponenten

6

Edukt 3

HCID 11208Isobutylene oxideHCID 91338Cyclohexanemethanol, alpha,3,3-trimethyl-HCID 16686341Ethyl aluminium dichloride

Produkt 1

HCID 120220122-[1-(3,3-Dimethylcyclohexyl)ethoxy]-2-methyl-1-propanolAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

At 0° C. under an atmosphere of nitrogen, 178 ml (321 mmol) of a 1.8 M solution of ethyl aluminium dichloride in toluene was slowly added to a stirred solution of 100 g (641 mmol) of 1-(3′,3′-dimethylcyclohexyl)ethanol and 55.4 g (769 mmol) of isobutylenoxide in 500 ml of cyclohexane. After complete addition, the cooling bath was removed, the reaction mixture was allowed to warm to room temperature, and stirring was continued at this temperature for 15 h. The reaction mixture was then poured into 1 L of brine, acidified with concentrated phosphoric acid, and thrice extracted with ether. The combined organic extracts were washed with brine and water, dried with sodium sulphate, and concentrated on a rotary evaporator. Distillation of the crude material (136 g) provided at 78-85° C./0.3 mbar 55.1 g (38%) of pure 2-[1′-(3″,3″-dimethylcyclohexyl)-ethoxy]-2-methylpropan-1-ol, while 60.4 g of starting material were recovered.

Aufarbeitung

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. additionThe reaction mixture was then poured into 1 L of brine
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with brine and water
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated on a rotary evaporator
  8. distillationDistillation of the crude material (136 g)

Quellen und Nachweise

ORD-Eintrag
ord-c2a06d032eff4e9d975790186acbc953
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390779B2

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