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

HRID 2212829Notes

Reaction equation

CCCCCC[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].CO[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH2:21][CH2:20][CH2:19]2.C1(C)C(C2C(C)=CC=CC=2)=CC=CC=1>>[CH3:13][C:12]1[CH:7]=[CH:8][C:9]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][CH:11]=1

Participants

Reactant 3

HCID 117972,2'-Dimethylbiphenyl

HCID 12388Tridecane

HCID 744146-Methoxytetralin2×

Product 1

HCID 111487746-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthaleneYield 61%

Conditions

Temperature: 60 °C

Procedure

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 A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M).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.

Workup

customIn a reaction flask was placed
customA sample was withdrawn
customquenched with an aqueous sodium citrate solution (1 M)
extractionThe aqueous solution was extracted with ethyl acetate

Sources & evidence

ORD record: ord-653ce31cff73432d96ed1580805266f5
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105467B2

Reaction notes

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