109089-77-2

124937-73-1

General procedure for the synthesis of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanol from 3-(2-methoxy-5-methylphenyl)-3-phenyl-1-propanol: Over a period of 2 hours, 0.5 kg of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanoic acid dissolved in 2.0 L of tetrahydrofuran was added slowly and dropwise to 0.105 kg of sodium borohydride containing a 0.5 L of tetrahydrofuran suspension. After the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Subsequently, 0.177 kg of methanesulfonic acid was slowly added over 1 hour. After addition, stirring was continued at room temperature for 1 hour. The reaction mixture was heated to 65-70°C and stirring was maintained for 8-10 hours. Upon completion of the reaction, it was cooled to 0-5 °C. The pH of the reaction mixture was adjusted to 2-3 with 0.25 L of aqueous 1 M hydrochloric acid, followed by extraction with ethyl acetate (1 L x 2). The organic layers were combined and washed sequentially with 2.0 L of water and 2.0 L of saturated saline. The solvent was removed by distillation under reduced pressure (30-40 mmHg) to give 3-(2-methoxy-5-methylphenyl)-3-phenyl-1-propanol (yield: 0.462 kg, 97% yield). The purity of the product was >95% by HPLC analysis.