Sulfuric Acid → 1-Methylbicyclo[2.2.1]heptan-2-ol

Participants

Reaction Steps

290.0 g (1.73M) of the acetate (III) obtained in 1-2) above dissolved in 300 ml of absolute diethyl ether was added to 65.2 g (1.7M) of lithium aluminum hydride suspended in 800 ml of absolute diethyl ether at room temperature under a nitrogen gas stream. Then the resulting mixture was heated under reflux for six hours and stirred at room temperature over night. Subsequently 500 ml of a 5% aqueous solution of sulfuric acid was slowly added to the reaction mixture with stirring under ice-cooling. The ether phase was collected and dried over anhydrous magnesium sulfate. After evaporation of the ether, the residue was distilled under reduced pressure to give 209 g (theoretical yield: 96%) of the aimed compound (IV) as a colorless oily material. b.p.: 83° C./20 mmHg.

Provenance & Evidence