Sodium Iodide → HCID 178509804, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsilyl chloride (305.6 g, 2.81 mols) was dropwise added to trans-4-methoxymethyl-1-(4-cyanophenyl)-cyclohexane (III) (322.5 g, 1.41 mol), NaI (421.6 g, 2.81 mols) 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 down to 10° C., filtering the reaction mixture by suction, pouring the mother liquor in ice water (2 Kg), extracting with chloroform (1.5 l), subjecting the resulting chloroform solution to twice washing with a 10% by weight aqueous solution of thiosulfate (0.5 l) and separating, further three times subjecting to washing with water (1 l) and separating, distilling off chloroform and three times recrystallizing the residue from toluene (300 ml) 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 solution a solution of trans-4-(4-cyanophenyl)cyclohexylcarbinol (IV) (107.6 g, 0.500 mol) obtained above (107.6 g, 0.500 mol) in dichloromethane (0.7 l) with stirring at room temperature, further agitating the mixture at room temperature for 1.5 hour, adding diethyl ether (1 l) to the resulting reaction solution and concentrating the supernatant according to florysil column chromatography to obtain trans-4-(4-cyanophenyl)cyclohexylcarboaldehyde (V) (101.2 g, 0.474 mol).

Provenance & Evidence