1. A solution of racemic trans-2-phenylcyclohexanol (100 g, 0.567 mol), chloroacetyl chloride (50 mL, 0.625 mol), and DMAP (300 mg, 0.0025 mol) in dichloromethane (250 mL) is rapidly stirred and heated under reflux for 6 h.  The reaction mixture is cooled, saturated sodium bicarbonate solution (350 mL) added, and the reaction mixture stirred for a further 3 h.

2. The organic layer is separated, dried over anhydrous potassium carbonate, filtered, and the filtrate concentrated under reduced pressure to afford a dark brown oil.

3. The oil is distilled through a 2-inch or 4-inch column packed with beads to give the racemic trans-2-phenylcyclohexyl chloroacetate (135 g, 94%) as a colorless liquid, b.p. 118-122°C at 0.3 mm.

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