Dicyclohexylcarbodiimide → HCID 22852144, compound

Participants

Reaction Steps

About 4.5 g (0.02 mol) of 3-fluoro-4-[(S)-2-methylbutoxy]benzoic acid (which can be prepared, for example, as described in EP-A 255 962 ), 5.0 g (0.02 mol) of 4-[4-(3-butenyl)phenylethyl]phenol, 4.1 g (0.02 mol) of dicyclohexylcarbodimide and 0.1 g of 4-dimethylaminopyridine were mixed in 40 ml of ether at room temperature. The mixture was first heated to reflux for 4 hours and then stirred at room temperature for 14 hours, and the resulting urea was filtered off. Washing was carried out first with 2N hydrochloric acid and then with NaHCO3 solution, and the ether phase was worked up. Column chromatography on Al2O3 with methyl tert-butyl ether/petroleum ether (1:2) as mobile phase resulted in 4.9 g of [4-[4-(3-butenyl)phenyl]ethylphenyl]-3-fluoro-4-[(S)-2-methylbutoxy]benzoate (yield 53.9%) which showed the following phase behavior: C 77 N* 86 I.

Provenance & Evidence