Dicyclohexylcarbodiimide → HCID 178442195, compound

Participants

Reaction Steps

(E)-trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexane carboxylic acid in an amount of 1.1 g (3.6 mmol), 0.7 g (4.3 mmol) of 4-pentylphenol, 0.1 g (1.1 mmol) of DMAP, and 20 ml of dichloromethane were mixed. To this mixture was added dropwise 4 ml of solution of 1.0 g (4.7 mmol) of DCC in dichloromethane while being cooled with ice in 5 min, and stirred as it was for 12 hours. Separated crystals were filtered off. To the filtrate was added 70 ml of toluene, washed with 2N-NaOH five times and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (eluent: toluene/heptane=1/1) to obtain 1.5 g of a crude (E)-4-pentylphenyl trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexanecarboxylate. This crude product was recrystallized from a mixed solvent of heptane/diethyl ether to obtain 1.2 g of the subjective compound (yield 74.7%).

Provenance & Evidence