Benzene, 1,2-dichloro-4-methyl- → 2-(4-Chlorobenzyl)phenol

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In a 50-ml, eggplant-shaped flask equipped with a magnetic stirrer and a reflux condenser were placed 6.6 g (30 mmole) of the 2-(4-chlorobenzylidene)cyclohexanone obtained in Example 12, 1.44 g (45 mmole) of sulfur and 12 ml of 3,4-dichlorotoluene in this order. The system was made vacuum using an aspirator and then returned to ordinary pressure using nitrogen; and this operation was repeated three times. The system was stirred for 4 hours at a bath temperature of 200° C. and then cooled to room temperature. 50 ml of toluene was added to the system, followed by extraction with 50 ml of a 10% aqueous sodium hydroxide solution; and this operation was repeated twice. The aqueous layer was washed with 50 ml of toluene. Then, 35% hydrochloric acid was added to the aqueous layer until the aqueous layer became acidic, followed by extraction with 50 ml of ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then subjected to vacuum distillation to remove ethyl acetate, to obtain 1.5 g of a brown oil. The oil was subjected to Kugel Rohr distillation to obtain 0.6 g of light yellow crystals. Yield: 9% The purity of the intended product in the crystal was 97.8% as measured by high performance liquid chromatography.

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