Dimethyl Sulfide → (E,E)-Farnesyl chloride

A solution of N-chlorosuccinimide (6.8 g, 50.9 mmol) in dry dichloromethane (338 ml) was cooled to -30° and dimethylsulfide (4.1 ml, 55.3 mmol) was added dropwise over 3 min. After 13 min., the cooling bath was removed and the mixture was stirred for 30 min. The mixture was cooled to -40° and a solution of (E,E)-farnesol (11.3 ml, 44 mmol) in 112 ml dichloromethane was added over 10 min. The cooling bath was removed and the mixture was stirred for 30 min. The temperature of the reaction mixture rose to 0° and a clear solution was obtained. After stirring for two more hours the solvent (about 400 ml) was removed on a rotary evaporator and the material was taken up in hexane (600 ml). The solution was washed with ice cold water (3×90 ml) and cold brine (2×35 ml) and then dried (MgSO4). The solvent was removed under vaccum at ambient temperature and finally dried under pump vaccum to give 11.0 g (100%) of title compound as a pale yellow liquid.

1. customthe cooling bath was removed
2. temperatureThe mixture was cooled to -40°
3. customThe cooling bath was removed
4. stirringthe mixture was stirred for 30 min
5. customrose to 0°
6. customa clear solution was obtained
7. customwas removed on a rotary evaporator
8. washThe solution was washed with ice cold water (3×90 ml) and cold brine (2×35 ml)
9. dry with materialdried (MgSO4)
10. customThe solvent was removed under vaccum at ambient temperature
11. customfinally dried under pump vaccum

ORD record

ord-f29d569763d14681b645396b59d337dd

Source dataset

uspto-grants-1993_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05177239