Ethyl Acetate → 3-Cyclohexyl-1-propanol

Participants

Reaction Steps

Lithium aluminum hydride (24.2 g, 0.64 mole) was slurried into 300 ml of dry ether (distilled from benzophenone ketyl, generated in situ from sodium and benzophenone). The slurry was cooled in an ice-water bath and a solution of 100 g (0.64 mole) of 3-cyclohexylpropionic acid (Bielstein 9:[2]13) in 250 ml of dry ether was slowly added. The resultant mixture was heated to reflux for 1 hr and then cooled in an ice-water bath. Ethyl acetate (100 ml) was slowly added to the mixture. This addition was followed by the addition of 24.2 ml of water, 24.2 ml of 15% aqueous sodium hydroxide solution and 72.6 ml of water. The mixture was filtered and the solvent was removed in vacuo. Distillation of this mixture at reduced pressure resulted in 71.6 g (78.7%) of pure 3-cyclohexylpropan-1-ol having the following physical characteristics:

Provenance & Evidence