Bromobenzene → 4-Pentyl-2,3,4,5-tetrahydro-1,1'-biphenyl

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Reaction Steps

In a 2,000 mL (inside volume) three-necked flask equipped with a reflux condenser, 700 mL of anhydrous THF and 27 g of magnesium shavings were charged, to which 160 g of bromobenzene were added dropwise at a speed to ensure continuous mild reflux. After the dropping was completed, the mixture was further stirred for 1 h. To the mixture, a solution of 170 g of 4-n-pentylcyclohexanone (available from Tokyo Chemical Industry Co., Ltd.) in 100 mL of THF was added at 50° C. The mixture was then refluxed for 2 h. The obtained reaction product liquid was cooled to room temperature, poured into an aqueous ammonium chloride solution and then extracted with benzene. The benzene solution was added with 1 g of p-toluenesulfonic acid and refluxed while removing water generated. When water was no longer distilled, the reaction mixture was cooled to room temperature, washed with an aqueous sodium hydrogen carbonate solution and then with an aqueous sodium chloride solution, dried and then concentrated. The residue was purified by silica gel column chromatography to obtain (4-n-pentylcyclohexenyl)benzene. The thus obtained product was dissolved in 1,000 mL of ethyl acetate and subjected to hydrogenation at 0.5 MPa using 2 g of 5% by mass-Pd/C as a catalyst. When a theoretical amount of hydrogen was consumed, the catalyst was separated by filtration. The resulting filtrate was concentrated to obtain 220 g of (4-n-pentylcyclohexyl)benzene. As a result of gas chromatographic analysis, it was confirmed that the (4-n-pentylcyclohexyl)benzene purity was 99.2% and the cis/trans molar ratio was 0.67.

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