1234 cm u2212 1 1171 cm u2212 1 1125 cm u2212 1 1108 cm u2212 1 1079 cm u2212 1 1047 cm u2212 1 1038 cm u2212 1 907 cm u2212 1 839 cm u2212 1 807 cm u2212 1 623 cm u2212 1 37 9 g u02dc 0 6 mol pulverized potassium hydroxide gt 85 is dissolved in 1250 ml 2 propanol with stirring and addition of nitrogen over approximately 30 minutes 100 g 0 196 mol raloxifene hydrochloride is added in small portions in such a way that temperature is kept below 30 u00b0 c after addition of raloxifene hydrochloride the deep red suspension is stirred for 30 45 minutes until a deep red solution appears reminiscence of insoluble product may be filtered off 260 ml of a solution of 62 76 g 0 6 mol malonic acid in 2 propanol water is added with violent stirring during 1 1 5 hours the mixture is now stirred further at room temperature for 18 hours and the precipitate is filtered off as white yellowish crystals the product is now washed 2 times with 40 ml 2 propanol and then dried in vacuo at 55 65 u00b0 c for 16 hours to give 182 4 g crude product the crude product is stirred with 912 ml of water for 3 hours and then filtered off and dried in vacuo at 55 65 u00b0 c for 16 hours to give 98 7 g 87 2 yield of crude product the crude product is boiled for 5 minutes in 500 ml 2 propanol and then cooled at 10 u00b0 c for 30 minutes the product is filtered.