Acetone → HCID 21717622, compound

Participants

Reaction Steps

A suspension of the derivative (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzonitrile (0.44 g, 1.20 mmol) in solution in alcoholic potassium hydroxide (0.94 g, 16.8 mmol KOH in 0.55 ml H2O and 3.3 ml EtOH) is heated to reflux under magnetic stirring for 4 hours. The progress of the reaction is followed by CCM (eluent acetone:hexane=10:90). The ethanol is evaporated in a rotary evaporator, the product taken up in water (50 ml), acidified with 1N HCl and extracted 3 times with ether. The ether phase is dried with MgSO4, filtered and evaporated to obtain, after washing with pentane and drying, 0.40 g of a white powder the acid (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzoic acid (yield=96%).

Provenance & Evidence