HCID 11195250, compound → HCID 20453110, compound

Participants

Reaction Steps

To a slurry of lithium aluminium hydride (6.39 g, 0.168 mol) in ether (250 ml), in an atmosphere of nitrogen and cooled in an ice-bath was added dropwise ethyl-3-cyclohexyl-3-hydroxy-butyrate (36 g, 0.168 mol) in ether (100 ml). After complete addition of the ester the resultant mixture was boiled at reflux for 1 hr, then cooled in an ice-bath. Excess lithium aluminium hydride was destroyed by successive dropwise addition of water (7 ml), 10% sodium hydroxide solution (7 ml) and water (21 ml). The reaction mixture was filtered, the filter cake washed with ether (2×100 ml) and the filtrate washed with saturated sodium chloride solution (1×250 ml) and then dried (Na2SO4). This mixture was filtered and the filtrate evaporated in vacuo to remove ether to give 3-cyclohexylbutane-1,3-diol (25 g) as an oil.

Provenance & Evidence