Trisammonium geranyl diphosphate

Geranyl chloride. To a flame-dried, 100-mL, three-necked, round-bottomed flask equipped with a magnetic stirrer, low temperature thermometer, rubber septum, and nitrogen inlet adapter, is added 1 .47 g (11 mmol) of N-chlorosuccinimide (Note 1) . The powder is dissolved in 45 mL of dry dichloromethane (Note 2), and the resulting solution is cooled to -30°C with a dry ice/acetonitrile bath. Freshly distilled dimethyl sulfide (0.87 mL, 0.74 g, 12 mmol) is added dropwise by syringe. The mixture is warmed to 0°C with an ice-water bath, maintained at that temperature for 5 min, and cooled to -40°C. To the resulting milky white suspension is added dropwise by syringe 1.54 g (10 mmol) of geraniol (Note 3) dissolved in 5 mL of dry dichlromethane.