P-Cresol → 6-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

In a reaction flask was placed NiCl2(PCy3)2 (36.6 mg, 0.0530 mmol), PCy3 (35.0 mg, 0.125 mmol), tridecane (166.7 mg, 0.904 mmol, as an internal standard), and 6-trimethylsiloxy-1,2,3,4-tetrahydronaphthalene (211.4 mg, 0.957 mmol). The solvent in the Grignard reagent (1 M in ether, 3.0 mmol) was exchanged with t-AmOMe (6.0 mL) and this solution added to the above catalyst mixture under a nitrogen atmosphere at room temperature. The resulting solution was stirred for several minutes at room temperature and then warmed to 60° C. for 15 hours. A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M). The resulting aqueous solution was extracted with ethyl acetate. GC analysis of the organic phase showed the presence of 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (0.637 mmol, 67% yield) and bitoluene (0.407 mmol) and p-methylphenol (0.223 mmol) in the reaction mixture.

Provenance & Evidence