Dimethyl Sulfate → 1-Methoxy-4-(trifluoromethyl)benzene

Participants

Reaction Steps

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.

Provenance & Evidence