2,2'-Dimethylbiphenyl → 6-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Conditions

Reaction Steps

In a reaction flask was placed NiCl2(PCy3)2 (51.0 mg, 0.0739 mmol), tridecane (251 mg, 1.364 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (264 mg, 1.627 mmol). The Grignard reagent (1 M in THF, 4.10 mmol) was added to this mixture under a nitrogen atmosphere at room temperature. The resulting solution was warmed to 60° C. for 15 hours. A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M). The 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 (0.993 mmol, 61% yield), bitoluene (0.52 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (0.471 mmol) in the reaction mixture.

Provenance & Evidence