Water → Cyclohexanol, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-

Participants

Reaction Steps

A suspension of lithium aluminum hydride (0.68 g, 0.018 mol) in anhydrous diethyl ether (50 mL) was stirred under nitrogen at 10° C. while 3,5-dimethyl-4-(3-methyl-2-butenyl) cyclohexanone (6.8 g, 0.035 mol) in anhydrous ether (15 mL) was added over a period of 30 minutes. The mixture was stirred at room temperature for 2 hours; then it was treated successively with H2O (0.7 mL), 15% NaOH (0.7 mL), and H2O (2.1 mL). The solution was filtered, dried (NaSO4), and concentrated to give the crude alcohol as a colorless oil. Kugelrohr distillation afforded 6.2 g of 3,5-dimethyl-4-(3-methyl-2-butenyl) cyclohexanol, bp 130° C./0.3 mm.

Provenance & Evidence