6335-76-8

64-17-5

141-82-2

100-52-7

6335-76-8

To a 500 mL three-necked flask was added 50 mL of ethanol, 9.3 g of malonic acid and 18.2 g of ammonium acetate, heated to 50°C, and 10.0 g of benzaldehyde was slowly added dropwise. After the dropwise addition, the reaction was heated to reflux. After the reaction was completed, the mixture was cooled to below 10°C and 40 g of thionyl chloride was slowly added dropwise. The mixture was heated to reflux for 16 hours, followed by distillation to remove ethanol. To the residue 50 mL of dichloromethane was added and the pH was adjusted to 6-7 with 5 N NaOH solution. the organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined and concentrated to give 14.2 g of colorless oily material, which was analyzed by HPLC for 98% purity and 78% yield.