Myristyl bromide → 7-Tetradecyloxy-4-methyl-coumarin

Participants

Reaction Steps

35.2 g (0.2 mole) of 7-hydroxy-4-methyl-coumarin, 27.6 g (0.2 mole) of potassium carbonate, 55.4 g (0.2 mole) of 1-bromotetradecane and 600.0 ml of dry dimethylformamide are stirred in a steam bath overnight. The mixture is cooled and extracted into 1.5 liters of diethyl ether. The ether layer is washed 5 times with saturated saline. It is dried (Na2SO4) and evaporated. The ether is replaced with 800 ml of hexane. The mixture is recrystallized therefrom, yielding 68.3g (92%) of 7-tetradecyloxy-4-methyl-coumarin, m.p. 61°-62° C.

Provenance & Evidence