Sulfuric Acid → 2,2,7,7-Tetramethylcycloheptan-1-ol

Participants

Reaction Steps

Lithium aluminium hydride (3.80 g, 0.1 mole) and dried diethyl ether (100 ml) were added to a one liter four-necked flask equipped with a mechanical stirrer, a dropping funnel, a thermometer, a reflux condenser and a calcium chloride tube and stirred at room temperature. A mixed solution of 2,2,7,7-tetramethylcycloheptanone (33.66 g, 0.2 moles)/dried diethyl ether (60 ml) was dropped into the mixture in 1 hour while stirring at room temperature. The mixture was stirred at room temperature for 1 hour. Subsequently, water (40 ml) and a 10% sulfuric acid aqueous solution (250 ml) were added in this order to the resulting reaction mixture to separate it into two layers. The resulting organic layer was washed twice with saturated saline solution (100 ml). The organic layer was dried over anhydrous magnesium sulfate and separated by filtration, followed by concentration and fractionation to obtain 33.45 g (yield 98.2%) of the captioned compound. This compound was a white solid having a woody, earthy, camphoraceous and hay-like odor.

Provenance & Evidence