110726-28-8

1256572-99-2

108-95-2

110726-28-8

To a 200 mL four-necked flask equipped with a dropping funnel, condenser tube, and mechanical stirrer were added 22.6 g (0.240 mol) of phenol, 0.7 g (equivalent to 3% of the mass of phenol) of toluene, and 0.5 mL of dodecyl mercaptan. The system was heated to 45 °C and protected by nitrogen for internal gas displacement, followed by saturation of the system with hydrogen chloride gas. 11.2 g (0.038 mol) of 4-[1-(4-acetoxyphenyl)-1-methylethyl]acetophenone prepared in Example 6 was dissolved in 11.2 g (0.119 mol) of phenol, and the resultant solution was added slowly dropwise through a dropping funnel into a reaction flask while maintaining the reaction temperature at 45°C for 1.5 hours. Hydrogen chloride gas was continuously passed during the addition. After the dropwise addition, the reaction mixture was stirred at 50°C for 21 hours to complete the reaction. At the end of the reaction, 50.0 g of toluene and 10.0 g of distilled water were added to the mixture, which was subsequently neutralized with 16% aqueous sodium hydroxide. The mixture was heated to 85 °C to dissolve the isolated crystals and separated to remove the aqueous layer. The organic layer was washed twice with distilled water and the aqueous layer was separated and removed after each wash. The organic layer was cooled to crystallize, and the precipitated crystals were collected by filtration and dried to give 13.6 g of white crystals, i.e., 1-[α,α-bis(4-hydroxyphenyl)ethyl]-4-[α-methyl-α-(4-hydroxyphenyl)ethyl]benzene, which was analyzed with a purity of 95.5% by high performance liquid chromatography. The yield of 4-[1-(4-acetoxyphenyl)-1-methylethyl]acetophenone was 83.2%.