[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[S].ClC1C=C(C)C=CC=1Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])=[CH:14][CH:15]=1In 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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