In order to investigate the acidic chlorinated compounds in pulp bleaching spent liquor, the lignin model compounds, coniferyl alcohol(mp $74^{circ}C$), ${omega}$-(2-methoxyphenoxy)-acetoguaiacone(mp $93^{circ}C$) and dehydrodiisoeugenol(mp $133^{circ}C$), were synthesized and chlorinated by chlorine in glacial acetic acid. From the chlorinated products, the following chlorine-containing aromatic compounds were identified by TLC. In coniferyl alcohol the chlorine-substituted compounds at 4-, 5-and 4,5-position of aromatic nucleus were identified and in ${eta}$-0-4 type the compounds substituted chlorine for alkyl group and/or hydrogen at land 1,4-position of aromatic nucleus expected to be formed by electrophilic displacement from ${omega}$-(2-methoxyphenoxy)-acetoguaiacone were not identified but the chlorine-substituted compounds at 4-, 5-, 6- and 5,6-position of aromatic nucleus were identified.