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

Participants

Reaction Steps

In a reaction flask was placed NiCl2(PCy3)2 (69.0 mg, 0.0999 mmol), PCy3 (57.8 mg, 0.206 mmol), tridecane (328 mg, 1.778 mmol, as an internal standard), and N,N-dimethyl-N-[2-(5,6,7,8-tetrahydronaphthalen-2-yloxy)ethyl]amine (409 mg, 1.867 mmol). The solvent in the Grignard reagent (1 M in ether, 6.0 mmol) was exchanged with diethoxymethane (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 95° C. for 15 hours. A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M) and was extracted with ethyl acetate. GC analysis of the organic phase showed the presence of 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (1.851 mmol, 99% yield) and bitoluene (0.654 mmol) and p-methylphenol (0.575 mmol) in the reaction mixture.

Provenance & Evidence