Tridecane → 4-Methoxybiphenyl

HRID 1786729Notes

Reaction equation

HRID 1786729 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].C1([Zn+])C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22](C#N)=[CH:21][CH:20]=1.CCCCCCCCCCCCC>C1COCC1.[Cl-].[Zn+2].[Cl-]>[C:1]1([C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 12388TridecaneHCID 701294-MethoxybenzonitrileHCID 178478979HCID 178478979, compoundHCID 178479830HCID 178479830, compound

Product 1

HCID 119434-MethoxybiphenylYield 45%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of zinc chloride (0.48 g; 3.5 mmol) in THF (5 mL) was treated at 0° C. with phenylmagnesium chloride (2.1 mL of a 1.40 M solution in THF; 3.0 mmol) and then stirred at room temperature for 30 min. The mixture of phenylzinc chloride thus obtained was then treated with a solution of 4-methoxybenzonitrile (0.27 g; 2.0 mmol), dichlorobis(trimethylphosphine)nickel (0.028 g; 5 mol %), and tridecane (0.18 g; 1.0 mmol; internal GC standard) in THF (2 mL) and heated at 60° C. for 8 h. A sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and ether. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 0.90 mmol (45% yield) of 4-phenylanisole, no 4-methoxybenzophenone imine, 0.38 mmol of anisole, 0.82 mmol of biphenyl, 0.23 mmol of 4,4′-dimethoxybiphenyl, and 0.09 mmol of 4-methoxybenzonitrile remaining in the reaction mixture.

Workup

  1. customthus obtained
  2. temperatureheated at 60° C. for 8 h
  3. customA sample was withdrawn
  4. customquenched in a mixture of 1 M sodium citrate (aq) and ether

Sources & evidence

ORD record
ord-0a84cd2ef25e4324b93bae980fdd2e4a
Source dataset
uspto-grants-2009_03
Patent number
US07507830B2

Reaction notes

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