but-3-enylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 220 g of toluene, 20.3 g (0.883 mol) of sodium dispersion was reacted with 46.5 g (0.413 mol) of chlorobenzene, to prepare phenyl sodium. The resultant toluene slurry was stirred for 2.5 hours under heat reflux. The thus-obtained black slurry was cooled, and then a toluene (40 g) solution containing 31.6 g (0.413 mol) of allyl chloride was added to the cooled slurry, keeping the reaction temperature in the range of from -10° C. to 0° C., and then the reaction mixture was allowed to stand, for aging, for 30 minutes at room temperature. After the reaction was completed, the reaction mixture was subjected to hydrolysis with 350 ml of water in the range of 5 to 20° C., and then the resultant organic layer was washed with 300 ml of water twice, according to a usual manner. Toluene was removed therefrom by atomospheric distillation, and the residual orange oil was subjected to distillation under reduced pressure in the same manner as in Example 7. As a result, 39.4 g (0.298 mol, yield 72.2%) of 4-phenyl-1-butene was given (purity 98.3%), and 6.3 g of a residue remained. under heat reflux The thus-obtained black slurry was cooled was added to the cooled slurry of from -10° C. to 0° C. the resultant organic layer was washed with 300 ml of water twice Toluene was removed by atomospheric distillation the residual orange oil was subjected to distillation under reduced pressure in the same manner as in Example 7

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A toluene (20 g) solution containing 2.58 g (0.025 mol, 2 mol %) of diisopropylamine was added to phenyl sodium, which had been prepared by reacting 60.0 g (2.610 mol) of sodium dispersion and 144.0 g (1.279 mol) of chlorobenzene in 800 g of toluene, at room temperature (about 20° C.), and then the reaction mixture was stirred for 2 hours. To the resultant greenish brown slurry was added a toluene (40 g) solution containing 98.0 g (1.280 mol) of allyl chloride, keeping the reaction temperature in the range of from -10° C. to 0° C., and then the reaction mixture was allowed to stand, for aging, for 1 hour at room temperature. After the reaction was completed, the reaction mixture was subjected to hydrolysis with 250 ml of sulfuric acid (5%) in the range of 5 to 20° C., and then the resultant solution was allowed to stand, then it was separated. The separated organic layer was washed with 200 ml of water twice, followed by gas chromatography analysis. It was identified that 4-phenyl-1-butene was given, at the yield of 96.4%. Further, the organic layer was condensed by atomospheric distillation, and the residue was further subjected to distillation under reduced pressure at 106° C./105 mmHg, to give 148.0 g of 4-phenyl-1-butene (1.119 mol, yield 87.5% on the basis of chlorobenzene. The term "yield" is hereinafter used in the same meaning as the above), followed by gas chromatography, for purity testing. As a result, it was found that the purity of 4-phenyl-1-butene was 98.7%. had been prepared of from -10° C. to 0° C. for aging, for 1 hour at room temperature it was separated The separated organic layer was washed with 200 ml of water twice condensed by atomospheric distillation the residue was further subjected to distillation under reduced pressure at 106° C./105 mmHg

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of m-chloroperbenzoic acid (43.5 g, 151 mmol) in chloroform (250 ml) was treated with 4-phenyl-1-butene (20 g, 151 mmol). The reaction was stirred for 1 hour at room temperature and washed with sodium bicarbonate, sodium sulfite, and saturated sodium chloride. The solution was dried over sodium sulfate and evaporated to dryness to afford 3,4-epoxybutylbenzene (100%). washed with sodium bicarbonate, sodium sulfite, and saturated sodium chloride The solution was dried over sodium sulfate evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 8 was repeated to form allyl magnesium chloride. The allyl magnesium chloride which flowed out of the flask through the branch was accumulated in a 3 L four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel placed under a nitrogen atmosphere. A mixed solvent of toluene and tetrahydrofuran dissolving allyl chloride was started to be added dropweise thereto. 2 hours after the start of the addition of the mixed solvent, 300 ml of a mixed solvent of toluene and tetrahydrofuran (a content of terahydrofuran 25% by weight) dissolving 156 g (1.23 mole) of benzyl chloride was added dropwise in the 3 L four-necked flask at a rate of 15 ml per hour at a temperature of 0 to 20° C. After the completion of the dropwise addition, the reaction mixture was stirred for 1 hour at the same temperature. After the completion of the reaction, an aftertreatment was effected in a similar manner to that in Example 1 to obtain 146.9 g (yield 90%, based on benzyl chloride) of 4-phenyl-1-butene which was a colorless liquid. An analysis of the product by gas chromatography indicated the purity of 98.7%. was accumulated in a 3 L four-necked flask equipped with a stirrer to be added dropweise was added dropwise in the 3 L four-necked flask at a rate of 15 ml per hour at a temperature of 0 to 20° C After the completion of the dropwise addition After the completion of the reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 1 was repeated except that 1.0 L of tetrahydrofuran was used as a solvent in place of the mixed solvent of 250 ml of tetrahydrofuran and 750 ml of toluene, and 127.0 g (yield 94%) of 4-phenyl-1-butene was obtained. The analysis of the product by gas chromatography indicated the purity of 98.0%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 1 was repeated except that 1.0 L of tetrahydrofuran was used as a solvent in place of the mixed solvent of 250 ml of tetrahydrofuran and 750 ml of toluene, and 127.0 g (yield 94%) of 4-phenyl-1-butene was obtained. The analysis of the product by gas chromatography indicated the purity of 98.0%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of m-chloroperbenzoic acid (43.5 g, 151 mmol) in chloroform (250 ml) was treated with 4-phenyl-1-butene (20 g, 151 mmol). The reaction was stirred for 1 hour at room temperature and washed with sodium bicarbonate, sodium sulfite, and saturated sodium chloride. The solution was dried over sodium sulfate and evaporated to dryness to afford 3,4-epoxybutylbenzene (100%). washed with sodium bicarbonate, sodium sulfite, and saturated sodium chloride The solution was dried over sodium sulfate evaporated to dryness