1-(4-chlorophenoxy)propan-2-ol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3.87 g of p-chlorophenol in 30 ml of tetrahydrofuran is added 1.2 g of sodium hydride (60% dispersion in oil). After one hour, 4.98 g of potassium iodide and 2.54 ml of 1-chloro-2-propanol in 10 ml of tetrahydrofuran is added. The mixture is heated at 80° C. for 18 hours. The mixture is chilled, poured into 300 ml of ice-water containing 3 ml of acetic acid. The mixture is extracted with dichloromethane and the extract washed with saturated sodium bicarbonate and sodium chloride solution. Drying (MgSO4) and removal of the solvent under reduced pressure gives 5.1 g of product as an oil. The mixture is chilled The mixture is extracted with dichloromethane the extract washed with saturated sodium bicarbonate and sodium chloride solution Drying (MgSO4) and removal of the solvent under reduced pressure

Conditions: temp:-8.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 37.4 g of 3-(p-chlorophenoxy)propan-2-ol and 41 ml of triethylamine in 500 ml of dichloromethane stirred and chilled at -8° C. is added dropwise 18.7 ml of methanesulfonyl chloride in 50 ml of dichloromethane. After stirring at -8° C. for 1 hour, the solution is washed with 350 ml portions of ice cold water, 1N HCl, saturated NaCl, saturated NaHCO3 and saturated NaCl. The organic layer is dried (MgSO4) and the solvent removed under reduced pressure to give 54 g of product as white crystals, mp 72°-78° C. the solution is washed with 350 ml portions of ice cold water, 1N HCl, saturated NaCl, saturated NaHCO3 and saturated NaCl The organic layer is dried (MgSO4) the solvent removed under reduced pressure