Dimethyl Sulfide → Geranyl chloride

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4.75 g (35.6 mmol) of N-chlorosuccinimide in 180 mL of dichloromethane at -35° C. (internal thermometer) under argon was added 3.3 mL (45.4 mmol) of dimethyl sulfide over 10 minutes. The mixture was allowed to warm to 0° C. for 15 minutes then cooled again to -35° C. A solution of 5.0 g (32.4 mmol) of (E)-3,7-dimethyl-2,6-octadien-1-ol (geraniol) in 25 mL of dichloromethane was added dropwise over 10 minutes. After addition, the reaction was allowed to warm gradually to 0° C. over 2 hours. After 1 hour at 0° C., the reaction was quenched with ice-cold water, diluted with 500 mL of hexane, and the organic layer was separated. The hexane extract was washed with water, brine, dried over MgSO4 and evaporated to provide 5.21 g (93%) of title compound in the form of a yellow liquid.

Provenance & Evidence