The Antipyretic Action of Para-Acetylaminophenylurethans

Abstract

hydrochloric acid, evaporated to dryness and extracted with hot alcohol. When the alcohol portion was evaporated to dryness, no residue was obtained.Trichloroacetylisodurene.-One-half gram of trichloroacetylisodurene was maintained at 120 °with 25 cc. of a solution of 40% sodium hydroxide in a sealed tube. Close observation showed only slow changes in the oil. At the end of thirteen hours considerable brown solid was found to have formed in the now discolored oil. At the end of twenty-six hours most of the oil had become dark brown or had changed over to the solid.The oil and solid mixture was filtered, washed with water and treated with acetone. Only a slight amount of light brown residue failed to dissolve. The acetone extract was evaporated to yield a small quantity of brown oil, presumably some of the starting material. The alkali filtrate was acidified with hydrochloric acid, evaporated to dryness and extracted with hot alcohol. This extract failed to yield any 2,3,4,6-tetramethylbenzoic acid, although a very small quantity of residue was obtained.