Dimethyl Sulfate → 5-[3-Hydroxy-4-(2-methoxybenzoyl)-2-propylphenoxy]pentanenitrile

Participants

Reaction Conditions

Reaction Steps

Five grams of 5-[3-hydroxy-4-(2-hydroxybenzoyl)-2-propylphenoxy]pentanenitrile, 11.7 g of potassium carbonate, and 1.42 ml of dimethyl sulfate in 50 ml of 2-butanone were stirred at reflux for approximately 18 hours. After cooling to 25° C., the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with one volume of water and one volume of a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated to dryness leaving a yellow oil which crystallized on standing. Recrystallization from ethyl acetate/hexane provided 4.38 g of the desired title product, m.p. 85°-86.5° C.

Provenance & Evidence