反应详情

4,4-Diphenylcyclohexanone 54.0 g was dissolved with stirring in tetrahydrofuran 700 ml, which was purified by dehydration, under nitrogen sealing and cooled with dry ice acetone. Then, a solution 200 ml of n-butyl lithium (1.6 mole/liter) in hexane was added dropwise for two hours. Two hours after adding, the ice bath was removed and the mixture was slowly heated to room temperature for four hours. The finish of the reaction was confirmed by liquid chromatography, then a saturated ammonium chloride aqueous solution 300 ml was poured into the reaction solution and the mixture was extracted with toluene 700 ml. The solution was washed with an aqueous solution of sodium chloride and toluene was removed with a rotary evaporator. Then, the residue was dissolved in toluene 400 ml, an ion exchange resin (Amberlist 15E, manufactured by ORGANO Co, Ltd.) 2.8 g was mixed, and the mixture was heated under reflux for three hours. The ion exchange resin was filtered off, toluene was removed with a rotary evapotator, the residue was dissolved in toluene/heptane 1/4 (v/v) and the solution was purified with a silica gel column to obtain 4,4-diphenyl-1-butylcyclohexene (containing 4,4-diphenyl-1-butylidenecyclohexane) 32.97 g.

1. customwhich was purified by dehydration, under nitrogen sealing
2. temperaturecooled with dry ice acetone
3. additionThen, a solution 200 ml of n-butyl lithium (1.6 mole/liter) in hexane was added dropwise for two hours
4. additionTwo hours after adding
5. customthe ice bath was removed
6. additiona saturated ammonium chloride aqueous solution 300 ml was poured into the reaction solution
7. extractionthe mixture was extracted with toluene 700 ml
8. washThe solution was washed with an aqueous solution of sodium chloride and toluene
9. customwas removed with a rotary evaporator
10. dissolutionThen, the residue was dissolved in toluene 400 ml
11. additionan ion exchange resin (Amberlist 15E, manufactured by ORGANO Co, Ltd.) 2.8 g was mixed
12. temperaturethe mixture was heated
13. temperatureunder reflux for three hours
14. filtrationThe ion exchange resin was filtered off
15. customtoluene was removed with a rotary evapotator
16. dissolutionthe residue was dissolved in toluene/heptane 1/4 (v/v)
17. customthe solution was purified with a silica gel column