A. 1-Phenyl-2,2,2-trichloroethanol. In a 1-l. round-bottomed-flask fitted with a mechanical stirrer, a thermometer, and a powder funnel is placed a solution of 212 g. (2.00 moles) of freshly distilled benzaldehyde in 400 g. (270 ml., 3.35 moles) of chloroform. The mixture is cooled in an ice bath, and 123 g. of commercial powdered potassium hydroxide is added with stirring at such a rate that the temperature of the solution does not exceed 45° (1–1.5 hours). The reaction mixture is stirred and kept at 40–50° for an additional hour and then poured into a solution of 60 ml. of sulfuric acid in 3 l. of water. The resulting two-phase mixture is transferred to a separatory funnel and extracted with three 250-ml. portions of chloroform (a small amount of insoluble, black resinous material is discarded). The combined organic layers are washed with three 100-ml. portions of aqueous 10% sodium carbonate, dried over anhydrous magnesium sulfate, and filtered into a 1-l. flask. The solvent is removed under reduced pressure on a hot water bath. The residue is transferred to a 250-ml. flask and distilled under reduced pressure to give 1-phenyl-2,2,2-trichloroethanol, b.p. 155–165° (26 mm.), 90–100° (0.5 mm.) (Note 1) and (Note 2). The yield is 170–180 g. (38–40%).

B. 1-p-Bromophenyl-1-phenyl-2,2,2-trichloroethane. In a 500-ml. round-bottomed flask fitted with a mechanical stirrer, a dropping funnel, and a thermometer are placed 136 g. (0.60 mole) of 1-phenyl-2,2,2-trichloroethanol and 120 g. (81 ml., 0.77 mole) of bromobenzene. The flask is cooled in an ice-water bath, and a mixture of 120 ml. of concentrated sulfuric acid and 50 ml. of oleum (20% SO₃) is added with stirring at such a rate that the temperature of the reaction mixture does not exceed 10° (ca. 45 minutes) (Note 3). The mixture is stirred for another 30 minutes at 10° and for 4–5 hours at room temperature. It is then poured with manual stirring onto 1 kg. of cracked ice, and the mixture is allowed to stand overnight. The precipitate (Note 4) is filtered, washed with water, and recrystallized from 300 ml. of ethanol (Note 5). The yield is 129–162 g. (59–74%), m.p. 95–96° (Note 6).

C. p-Bromodiphenylmethane. A 2-l. three-necked flask fitted with a distillation condenser, a thermometer, and an efficient mechanical stirrer is charged with 1.1 l. of diethylene glycol (Note 7) and a solution of 190 g. of potassium hydroxide in 100 ml. of water. The mixture is stirred, and water is distilled until the internal temperature reaches 180°. The resulting solution is allowed to cool to 100° or below, and 146 g. (0.40 mole) of 1-p-bromophenyl-1-phenyl-2,2,2-trichloroethane (Note 8) is added. The condenser is set for reflux, and the mixture is stirred and heated to boiling for 5 hours (Note 9). The hot solution is then poured onto 3 kg. of cracked ice, and the mixture is allowed to stand overnight. The oily layer is separated and dissolved in ether (any insoluble material is discarded), and the aqueous layer is extracted with 250 ml. of ether. The combined ethereal solution and extracts are dried over calcium chloride and filtered. The ether is removed under reduced pressure on a hot water bath. The product is distilled under reduced pressure; b.p. 120–130° (3 mm.), 155–163° (13 mm.) (Note 10), n²⁴D 1.6028, d₂₄24 1.342. The yield is 74–79 g. (75–80%) (Note 11).