Sodium Iodide → HCID 178509804, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsilyl chloride (305.6 g, 2.81 mol) was dropwise added to trans-4-methoxymethyl-1-(4-cyanophenyl)-cyclohexane (III) (322.5 g, 1.41 mol), sodium iodide (421.6 g, 2.81 mol) and acetonitrile (2.5 l) in nitrogen atmosphere with stirring at 35° C. over 30 minutes, followed by agitating the mixture for 20 minutes, cooling the reaction mixture down to 10° C., filtering it by suction, pouring the filtrate in ice water (2 Kg), extracting with chloroform (1.5 l), twice washing the resulting chloroform solution with a 10% by weight aqueous solution of sodium thiosulfate (0.5 l), three times washing with water (1 l), distilling off chloroform from the chloroform solution and three times recrystallizing the residue from toluene (300 m) for purification to obtain trans-4-(4-cyanophenyl)cyclohexylcarbinol (IV) (182.5 g, 0.848 mol) having a m.p. of 108.5°-110.8° C. On the other hand, pyridinium chlorochromate (161.7 g, 0.750 mol) was added to dichloromethane (1 l), followed by instantaneously adding to the mixture, a solution of trans-4-(4-cyanophenyl)cyclohexylcarbinol (IV) (107.6 g, 0.500 mol) obtained above, in dichloromethane (0.7 l) with stirring at room temperature, further agitating the mixture at room temperature for 1.5 hours, adding diethyl ether (1 l) to the reaction mixture, and concentrating the supernatant by passing it through a Florisil chromatography column to obtain trans-4-(4-cyanophenyl)cyclohexylcarbaldehyde (V) (101.2 g, 0.474 mol).

Provenance & Evidence