Hydrochloric Acid → (2-Hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane

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In a 300 ml eggplant-type flask equipped with a Dimroth condenser, 10.3 g (0.057 mol) of intermediate 2-(hydroxymethyl)-5-t-butylphenol and 10.2 g (0.062 mol) of 2-t-butyl-4-methylphenol were suspended in 60 ml of water. To this suspension, an aqueous solution having 10.2 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 a temperature of from 100° to 110° C. and stirred at that temperature for 17.5 hours. The reaction mixture was cooled to room temperature, acidified by concentrated hydrochloric acid and then extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and then dried over anhydrous magnesium sulfate. From the solution having the anhydrous magnesium sulfate removed, ethyl acetate was distilled off, and the obtained residue was roughly separated by silica gel column chromatography. To the obtained brown highly viscous oil, n-hexane was added and left to stand still to obtain 6.7 g (0.021 mol, yield: 36.0%) of (2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane as a white solid. By 1HNMR, this solid was confirmed to be the desired product.

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