ChemicalBook CAS DataBase List [1R-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

[1R-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one synthesis

7synthesis methods

Product Name:[1R-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
CAS Number:473-62-1
Molecular formula:C10H16O
Molecular Weight:152.23

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[1R-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

473-62-1
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Yield:473-62-1 93.4%

Reaction Conditions:

with Jones reagent in acetone at 0; for 3 h;

Steps:

165

Preparation 165(lR,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept; Jones reagent: add a mixture of 9 ml of H₂SO₄ and 40 ml of H₂0 to a solution of Cr₂0₃ (15.0 g, 0.15 mol) in H₂0 (20 mL) at 0 °C.Add dropwise the above Jones reagent to a solution of (lR,2R,3R,5S)-2,6,6- trimethylbicyclo[3.1.1]heptan-3-ol (23.1 g, 0.15 mol) in acetone (100 mL) over a period for 2 hours at 0 °C. Stir the resultant mixture for additional 1 hour. Dilute the mixture with 100 mL of water and then extract the aqueous mixture with ether (50 mL X3). The combined organic layers are washed with brine (20 mL), dried over Na₂SC>4, filtered, and concentrated under vacuum to give crude (lR,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one as pale yellow oil (21.3 g, yield: 93.4%), MS (m/z): 151 (M-1).

References:

WO2012/100423,2012,A1 Location in patent:Page/Page column 76-77