O[CH2:2][C:3]1[C:8]([OH:9])=[C:7]([CH3:10])[CH:6]=[C:5]([CH3:11])[CH:4]=1.[C:12]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[OH:23])([CH3:15])([CH3:14])[CH3:13].[OH-].[Na+].Cl>O>[OH:23][C:17]1[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:21][C:20]([CH3:22])=[CH:19][C:18]=1[CH2:10][C:7]1[CH:6]=[C:5]([CH3:11])[CH:4]=[C:3]([CH3:2])[C:8]=1[OH:9]
In a 300 ml eggplant-type flask equipped with a Dimroth condenser, 10.4 g (0.068 mol) of intermediate 6-(hydroxymethyl)-2,4-dimethylphenol and 11.6 g (0.071 mol) of 2-t-butyl-4-methylphenol were suspended in 50 ml of water. To this suspension, an aqueous solution having 10.3 g (0.26 mol) of sodium hydroxide dissolved in 50 ml of water, was added, and the mixture was stirred by a magnetic stirrer. This mixture was heated to 100° C. and stirred at that temperature for 12 hours. The reaction mixture was cooled to room temperature, then acidified by concentrated hydrochloric acid and extracted with toluene. The obtained toluene solution was washed with water and then dried over anhydrous magnesium sulfate. From the solution having the anhydrous magnesium sulfate removed, toluene was distilled off, and the obtained residue was separated by silica gel chromatography to obtain 10.6 g (0.036 mol, yield: 51.9%) of (2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-3,5-dimethylphenyl)methane as a brown highly viscous liquid. By 1HNMR, the liquid was confirmed to be the desired product.
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