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ChemicalBook CAS DataBase List 4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene synthesis

12synthesis methods
-

Yield:768-56-9 93%

Reaction Conditions:

with sulfuric acid;nitrogen in tetrahydrofuran;water;iodine

Steps:

2 Example 2
Example 2 Into a 3 L four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, 37.45 g (1.54 mole) of metal magnesium in a shaved form and 0.1 g of iodine were charged. After the flask was filled with nitrogen, 500 ml of tetrahydrofuran and 500 ml of tert.-butyl methyl ether were added. The flask was sufficiently cooled on an ice bath, and then 118 g (1.54 mole) of allyl chloride was added dropwise at a temperature of 0° to 20° C. over a period of 2 hours with stirring. The reaction mixture obtained was filtrated at a room temperature under a nitrogen atmosphere to remove unreacted magnesium. The flitrate was transferred to another 3 L four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel. Then 130 g (1.03 mole) of benzyl chloride was added dropwise at the same temperature over a period of 30 minutes, followed by stirring the mixture at the same temperature for 4 hours. After the completion of the reaction, the reaction mixture was added to 300 ml of 5% sulfuric acid at a temperature of 0° to 10° C., followed by stirring for 30 minutes. Thereafter it was allowed to stand and phase-separated. The resulting oil layer was washed with 200 ml of water, followed by phase-separation. The resulting oil layer was distilled in the similar manner to that in Example 1 to obtain 125.7 g of 4-phenyl-1-butene (yield 93%). An analysis of the product by gas chromatography indicated the purity of 98.0%.

References:

Sumitomo Chemical Company, Limited US5637736, 1997, A

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