تفاعل #335751

معادلة التفاعل

dimethylsulfide

N-chlorosuccinimide

(E,E)-farnesol

→

title compound

المردود 103.8%

(E,E)-Farnesyl chloride

المردود 103.8%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe cooling bath was removed
2. 2
   درجة الحرارةThe mixture was cooled to -40 °
3. 3
   أخرىThe cooling bath was removed
4. 4
   workup.STIRRINGthe mixture was stirred for 30 min
5. 5
   أخرىrose to 0°
6. 6
   أخرىa clear solution was obtained
7. 7
   أخرىwas removed on a rotary evaporator
8. 8
   غسيلThe solution was washed with ice cold water (3×90 ml) and cold brine (2×35 ml)
9. 9
   تجفيفdried (MgSO4)
10. 10
    أخرىThe solvent was removed under vacuum at ambient temperature
11. 11
    أخرىfinally dried under pump vacuum

الإجراء التجريبي

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 vacuum at ambient temperature and finally dried under pump vacuum to give 11.0 g (100%) of title compound as a pale yellow liquid.

المصدر