Alkyl ethers of m- and p-aminophenols were prepared and antibacterial action of their hydrochlorides against tubercle bacilli was tested in Kirchner medium. In the alkylation of acetylaminophenol, the best result was obtained by the use of alkyl p-toluenesulfonate as the alkylating agent. The reactivity of the three isomers of acetylaminophenol was in the order of para, meta, and ortho. The compounds synthesized were, ethyl, butyl, hexyl, octyl, decyl, dodecyl, tetradecyl, and hexadecyl ethers of m-aminophenols, and butyl, octyl, dodecyl, and tetradecyl ethers of p-aminophenols. The antibacterial action of the hydrochlorides of these amines against tubercle bacilli was generally low but there was found a correlationship between the size of the alkyl group and the antibacterial action, such action increasing with the number or carbon atoms in the alkyl, reaching the maximum at around C12, and gradually decreasing over that number.
