1-Methylnaphthalene → 1-methyl-4-(4-methylnaphthalen-1-yl)naphthalene

HRID 1979660Notes

Reaction equation

HRID 1979660 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1>C(OP(OCCCC)(OCCCC)=O)CCC.OS(O)(=O)=O>[CH3:5][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:1]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 70021-Methylnaphthalene

Product 1

HCID 6247741-methyl-4-(4-methylnaphthalen-1-yl)naphthaleneYield 4.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 31357Tributyl PhosphateSolvent

Procedure

2 g (14 mmol) of 1-methylnaphthalene in 2 ml of tributylphosphate was allowed to react with electrochemically produced Ag(II) sulphate at 23° C. The electrolyte solution was composed of 0.02M Ag(I) sulphate in 1.5M H2SO4. The reaction was run for 26 hours at 200 mA. The organic material isolated from the run was placed on a silica gel column, which was eluted with petroleum ether (bp=60°-80° C.) then with a solution of 1% ether in petroleum ether. From this column there were obtained 1.2 g (8.4 mmol, 60%) of starting material and 92 mg (0.32 mmol, 4.6%) of 4,4'-dimethylbinaphthyl.

Workup

  1. customThe organic material isolated from the run
  2. washwas eluted with petroleum ether (bp=60°-80° C.)

Sources & evidence

ORD record
ord-7f14e0845bdf4610852bef6fc244ad15
Source dataset
uspto-grants-1984_11
Patent number
US04482438

Reaction notes

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