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

HRID 2212836Notes

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 35%

Procedure

In a reaction flask was placed NiCl2(dcpb) (38.0 mg, 0.0655 mmol), dcpb (34.6 mg, 0.0768 mmol), tridecane (164.5 mg, 0.892 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (169.3 mg, 1.044 mmol). The solvent in the Grignard reagent (1 M in ether, 3.0 mmol) was exchanged with t-AmOMe (5.0 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 A sample was withdrawn and quenched into saturated aqueous ammonium chloride and was extracted with ethyl acetate. GC analysis of the organic phase showed the presence of 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (0.363 mmol, 35% yield), bitoluene (0.216 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (0.429 mmol) in the reaction mixture.

Workup

customIn a reaction flask was placed
additionthis solution added to the above catalyst mixture under a nitrogen atmosphere at room temperature
temperaturewarmed to 80° C. for 15 hours
customA sample was withdrawn
customquenched into saturated aqueous ammonium chloride
extractionwas extracted with ethyl acetate

Sources & evidence

ORD record: ord-5984138a881a4541aeb810d2461b09ed
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105467B2

Reaction notes

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