Example 4 from U.S. Pat. No. 4,835,284 is duplicated. 97% sodium hydroxide (8.2 g) is added and dissolved in a mixture of methanol (60 ml) and water (20 ml). 2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene (11.6 g) is then added to the resultant solution at 50° to 60° C. over 30 minutes while stirring, and thereafter 2,3-dichloro-1,4-naphthoquinone (0.3 g) and 9-fluorenone (0.4 g) are added to the solution. Glucose (8 g) is then added to the resultant mixture at 40° to 50° C. over two hours, and the mixture is stirred for one hour at the same temperature. As this result, almost all of the azobenzene disappears to produce 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide. The system is heated, and is stirred at 66° to 68° C. (boiling point) for 5 hours. As this result, the N-oxide disappears. Thereafter, water (50 ml) is added to the reaction liquor, and the resultant reaction liquor is neutralized with 62% sulfuric acid (10 g) to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with hot water of 60° to 70° C. and further with a small amount of methanol. The washed crystal is then dried, thus obtaining 8.7 g of 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole having a melting point of 138° to 140° C. at the yield of 82.9%. One can see that the reaction using an aromatic ketone takes over 71/2 hours.
