3-Cyclohexene-1-carboxaldehyde → 2-(3-Cyclohexen-1-yl)-2-hydroxyacetonitrile

Participants

Reaction Conditions

Reaction Steps

3-Cyclohexene-1-carbaldehyde (11.7 ml. 0.1 mole) and sodium bisulfite (15.5 g., 0.15 mole) were combined with 150 ml. of H2O and heated at 50°-60° C. for 2 hours. The mixture was cooled to 5° C. and added dropwise over 10 minutes to a cold solution of KCN (19.5 g., 0.3 mole) in 50 ml. H2O. The mixture was warmed to 20° C., KCN (6.5 g., 0.1 mole) added as a solid, stirred for 10 minutes, and product extracted into 100 ml. ethyl acetate. The ethyl acetate extract was washed with brine and evaporated to yield title product as an oil, 8.5 g., Rf (5:1 hexane:ethyl acetate/5% CH3CO2H) 0.5.

Provenance & Evidence