2- Phenylcyclohexyl chloroacetate, trans

B. Racemic trans-2-phenylcyclohexyl chloroacetate. A 1-L, round-bottomed flask equipped with a magnetic stirrer and a condenser is charged with 100 g (0.567 mol) of racemic trans-2-phenylcyclohexanol, 50 mL (0.625 mol) of chloroacetyl chloride (Note 9), 300 mg (0.0025 mol) of 4-dimethylaminopyridine (DMAP) (Note 10) and 250 mL of dichloromethane. This mixture is rapidly stirred and heated at reflux for 6 hr. The mixture Is cooled and a solution of 350 mL of saturated sodium bicarbonate is carefully added to the rapidly stirring mixture (Note 11). Stirring is maintained for 3... 

D. (+)-(1S,2R)-trans-2-Phenylcyclohexanol. A 500-mL, round-bottomed flask is charged with a mixture of 52.0 g (0.206 mol) of (+)-(1S,2R)-trans-2-phenylcyclohexyl chloroacetate, 250 mL of 2 N sodium hydroxide, and 100 mL of methanol and then stirred at reflux for 3 hr. TLC analysis (Note 24) indicates complete reaction. The mixture is cooled to room temperature, adjusted to pH 7 with -35 mL of 3 N sulfuric acid and poured into 500 mL of water. The mixture is extracted with two 150-mL portions of dichloromethane and the organic layer is dried over anhydrous sodium sulfate and concentrated on a rotary evaporator (35°C) to afford 37.0 g of a colorless solid. Recrystallization from 100 mL of petroleum elher (30-60°C) at -20°C gives in... 

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