Imidazole → 1H-Imidazole, 1-(1-naphthalenylmethyl)-

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Reaction Steps

A mixture of imidazole (15.4 g) and 1-chloromethyl-naphthalene (14.9 ml, 0.1 mol) in 200 ml of methylene chloride was stirred at room temperature overnight. The mixture was stirred with 200 ml of water, the layers were separated, the organic layer was washed with water (2×200 ml), the resulting solids were removed by filtration and then the organic layer was stirred with 30 ml of conc. HCl and 200 ml of water. The methylene chloride layer was discarded, and the aqueous layer was extracted with 100 ml of ether. The above aqueous layer was basified with 3N NaOH solution, extracted with methylene chloride, and the organic layer was dried over magnesium sulfate. The above organic solution was concentrated in vacuo to afford 13.58 g of 1-(1-naphthylmethyl)imidazole.

Provenance & Evidence