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

Participants

Reaction Steps

In a reaction flask was placed NiCl2(PCy3)2 (49.0 mg, 0.0710 mmol), PCy3 (44.0 mg, 0.157 mmol), tridecane (333 mg, 1.806 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (222 mg, 1.368 mmol). The solvent in the Grignard reagent (1 M in ether, 3.70 mmol) was exchanged with i-Pr2O (8.0 mL) and MTBE (2.0 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 80° 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 A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M).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 (1.030 mmol, 75% yield) and 6-methoxy-1,2,3,4-tetrahydronaphthalene (0.131 mmol) and bitoluene (0.376 mmol) and m-methylphenol (0.220 mmol) in the reaction mixture.

Provenance & Evidence