Imidazole → 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 56.7 g (0.26 mol) of 1-chloro-4-chlorophenyl-2-butanol (J. of Medicinal Chemistry, 1978. Vol. 21. No. 8. p. 842) in 200 ml of toluene 36.2 g (0.9 mol) of sodium hydroxide dissolved in 100 ml of water, 6.4 g (0.028 mol) of benzyltriethyammonium chloride and 35.2 g (0.51 mol) of imidazole (III) are added. The reaction mixture is heated at 93-95° C. for one hour then the temperature is returned to about 60° C., the phases are separated and to the organic layer water (100 ml) is added. The mixture is first stirred at 22-25° C. for 1 hour then at 0-5° C. for two hours. The crystals are separated by filtration, washed with water (2×35 ml) of 0-5° C. to yield 74 g of wet (1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) which is dried at maximum 50° C. in vacuo to give 61.6 g (95%) of the product. Recrystallization from ethyl acetate gives 52.4 g (85%) of dry product melting at 104-106° C.

Provenance & Evidence