Formate → 1,5-Dimethylbicyclo(3.2.1)octan-8-one

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Reaction Steps

A quantity of 56 ml of 98% H2SO4 was added dropwise with stirring and cooling to a solution of 67 g of CrO3 (0.67 mol) in 100 ml of ice water. The mixture was diluted with water to a total volume of 200 ml. The solution obtained was added with stirring to a solution of 54.6 g (0.32 mol) of the formate of 1,5-dimethylbicyclo [3,2,1] octan-8-ol and 0.5 g of tetrabutylammonium chloride in 120 ml of acetone at such a rate that the temperature of the reaction mixture was 35°-40° C. The mixture was stirred for a further 2 hours at 35° C. and subsequently, the acetone solution was separated from the bottom layer. The latter was extracted a few times with acetone and the extracts were added to the acetone solution. The mixture was washed with a saturated K2CO3 solution and subsequently dried on K2CO3. The acetone was distilled off and the residue was vacuum-distilled. The distillate was dissolved in 100 ml of pentane and refluxed for 10 minutes after the addition of 50 ml of a 25% KOH solution in methanol. The pentane solution was washed with water and dried on Na2SO4. After the pentane had been distilled off, the residue was vacuum-distilled after the addition of 1 g of sodium. A quantity of 41 g of 1,5-dimethylbicyclo [3,2,1] octan-8-one was obtained having a boiling point of 104° C. at a pressure of 22 mm Hg.

Provenance & Evidence