4-Chlorobenzophenone → 1-[(Benzyloxy)methyl]-alpha-(p-chlorophenyl)-alpha-phenylimidazole-2-methanol

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Reaction Steps

To a solution of 11.8 g. of 1-[(benzyloxy)methyl]imidazole in 100 ml. of anhydrous tetrahydrofuran and 50 ml. of anhydrous diethyl ether a solution of 38 ml. of a 20% butyllithium suspension in hexane dissolved in 75 ml. of anhydrous diethyl ether was added drop-wise with stirring at room temperature. Thereafter a solution of 14.6 g. of 4-chlorobenzophenone in 100 ml. of anhydrous tetrahydrofuran and 50 ml. of anhydrous diethyl ether was added drop-wise at room temperature. The mixture was kept for three hours and then extracted with a dilute acid solution. The acidic aqueous layer was made alkaline with 2 N sodium hydroxide solution and extracted with diethyl ether. Part of the ether was removed by evaporation and the residue washed with water. The ether solution was again concentrated and the desired compound crystallised from a mixture of toluene and petroleum ether (boiling range 28°-40° C.). Melting point of the product was 114.5°-117° C.

Provenance & Evidence