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

HRID 2212831Notes

Reaction equation

HRID 2212831 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>C1(C)C=CC=CC=1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=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

6

Reactant 3

HCID 117972,2'-DimethylbiphenylHCID 12388TridecaneHCID 744146-Methoxytetralin2×

Product 1

HCID 111487746-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthaleneYield 29%

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

The Grignard reagent (1 M in ether, 5.0 mmol) was placed under vacuum to remove all volatiles. Toluene (5.0 mL) was then added to the Grignard reagent. In a separate reaction flask was placed NiCl2(PPh3)2 (62.0 mg, 0.0948 mmol), tridecane (282 mg, 1.532 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (334 mg, 2.059 mmol). The Grignard reagent in toluene was then transferred to this mixture under a nitrogen atmosphere at room temperature. The resulting solution was warmed to 110° 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 A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M).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 (0.598 mmol, 29% yield), bitoluene (0.419 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (1.043 mmol) in the reaction mixture.

Workup

  1. customto remove all volatiles
  2. additionToluene (5.0 mL) was then added to the Grignard reagent
  3. customIn a separate reaction flask
  4. customwas then transferred to this mixture under a nitrogen atmosphere at room temperature
  5. customA sample was withdrawn
  6. customquenched with an aqueous sodium citrate solution (1 M)
  7. extractionThe aqueous solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-e3da3ca866824d6896d7fec6e2832f2e
Source dataset
uspto-grants-2006_09
Patent number
US07105467B2

Reaction notes

Loading…