4-Chlorophenol → 1-(4-Chlorophenoxy)-3-methyl-4-isoquinoline Acetic Acid

Participants

Reaction Steps

A mixture of 1-chloro-3-methyl-4-isoquinoline acetic acid (237 mg., 1.01 mmol) prepared as in Example 8, 4-chlorophenol (260 mg., 2.02 mmol), and potassium tert-butoxide (226 mg., 2.02 mmol) were heated at 100° for 3 hr. After cooling the mixture was diluted with ethyl acetate and water and acidified to pH 1-2. The separated aqueous phase was extracted with 20 ml. ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and vacuum evaporated to a brown oil. Chromatography of this on silica gel eluted with ethyl acetate gave a pale yellow solid; 80 mg., 24%, mp 192°-195° d.

Provenance & Evidence