Dicyclohexylcarbodiimide → HCID 178444281, compound

Participants

Reaction Steps

A mixture of 1.0 g of trans-4-(p-cyanophenyl)cyclohexanol, 1.75 g of 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid, 1.2 g of dicyclohexylcarbodiimide and 98 mg of 4-(dimethylamino)pyridine in 60 ml of dichloromethane was stirred at room temperature for 18 hours under argon gasification. The beige suspension was subsequently filtered (rinsing with dichloromethane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.1 g) on silica gel with toluene yielded 1.2 g (45%) of pure 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid trans-4-(p-cyanophenyl)cyclohexyl ester. Recrystallization from ethyl acetate/acetone (vol. 1:4) gave white crystals of m.p. (C-N) 148.6° C. and cl.p. (N-I) 347° C.; purity 99.6%.

Provenance & Evidence