反应详情

25.0 g (0.15 moles) of 4-(trifluoromethyl)phenol and 23.5 g (0.17 moles) of potassium carbonate were mixed in 80 ml of acetone in a 200 ml three-necked flask. The flask was equipped with a reflux condenser, a dropping funnel and a thermometer and was connected with a calcium chloride tube for shielding the flask against moisture of the outside. After the mixing, 21.4 g (0.17 moles) of dimethyl sulfate were added at a temperature of not higher than 30° C. in a dropwise manner to the mixture under stirring. After that, the reaction mixture was refluxed at reflux temperature of acetone for 5 hrs. After completing the reaction, the reaction liquid was cooled down to room temperature. The resulting precipitates (solid) were separated by filtration. The obtained filtrate was concentrated by an evaporator. To the resulting residue 100 ml of water and 100 ml of n-hexane were added, thereby extracting the target product into the n-hexane layer. To the resulting water layer 50 ml of n-hexane were added, thereby conducting an extraction again. The resulting two n-hexane layers were combined together, followed by washing with 80 ml of 2 mol/L sodium hydroxide aqueous solution. The resulting n-hexane layer was washed two times with 50 ml of water. The obtained n-hexane layer was dried with magnesium sulfate anhydride, followed by concentration by an evaporator and then by removal of hexane by distillation under reduced pressure, thereby obtaining 22.8 g (0.13 moles) of oily 4-(trifluoromethyl)anisole (isolation yield: 84.0%). This product was found to have the following properties.

1. customThe flask was equipped with a reflux condenser, a dropping funnel
2. customa thermometer and was connected with a calcium chloride tube
3. temperatureAfter that, the reaction mixture was refluxed
4. customthe reaction
5. customthe reaction liquid
6. customThe resulting precipitates (solid)
7. customwere separated by filtration
8. concentrationThe obtained filtrate was concentrated by an evaporator
9. additionTo the resulting residue 100 ml of water and 100 ml of n-hexane were added
10. extractionextracting the target product into the n-hexane layer
11. additionTo the resulting water layer 50 ml of n-hexane were added
12. extractionan extraction again
13. washby washing with 80 ml of 2 mol/L sodium hydroxide aqueous solution
14. washThe resulting n-hexane layer was washed two times with 50 ml of water
15. dry with materialThe obtained n-hexane layer was dried with magnesium sulfate anhydride
16. concentrationfollowed by concentration by an evaporator
17. customby removal of hexane
18. distillationby distillation under reduced pressure