Hydrochloric Acid → 4,4'-(1,2-Ethanediyl)bis(2,6-bis(1,1-dimethylethyl)phenol

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The electrolysis cell was charged with 300 milliliters of 10 percent aqueous acetonitrile and 6.9 grams (0.03 mole) of tetraethylammonium perchlorate. Nitrogen gas was passed through the system while 4.4 grams (0.02 mole) of 2,6-di-t-butyl-4-methylphenol, and 0.108 gram (0.002 mole) of sodium methoxide were added. The electrolysis was conducted at ambient temperatures under a nitrogen atmosphere at an anode potential of +0.35 volt (versus the saturated calomel electrode). The initial current of 210 milliamperes decreased to 16 milliamperes over the 10-hour electrolysis period. Upon completion of the electrolysis, the reaction mixture was acidified with 2.0 milliliters of concentrated hydrochloric acid and allowed to stand overnight (about 15 hours). The graphite felt anode was washed with two 50-milliliter portions of chloroform to remove the precipitate which had collected thereon during both the electrolysis and the standing period. The chloroform solution was dried over anhydrous magnesium sulfite and evaporated in vacuo to yield pure crystals of 1,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)ethane (3.88 grams, 88.6 percent), melting point 170°-171° C.

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