Sodium Iodide → p-Tolunitrile

HRID 2253512Notes

Reaction equation

HRID 2253512 reaction equation
[C:1]([Cu])#[N:2].[Na+].[I-].CN[C@@H]1CCCC[C@H]1NC.ClC1C=CC=CC=1.CCCCC[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(OCC)(=O)C>[CH3:34][C:33]1[CH:28]=[CH:29][C:30]([C:1]#[N:2])=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7964ChlorobenzeneHCID 8182DodecaneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178418546HCID 178418546, compound

Product 1

HCID 7724p-TolunitrileYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
130 °C

Procedure

A Schlenk tube was charged with CuCN (108 mg, 1.21 mmol), NaI (150 mg, 1.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (190 μL, 1.21 mmol) and 4-chlorobenzene (0.95 mL, 8.01 mmol) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 20 h. The resulting black suspension was allowed to reach room temperature. Ethyl acetate (3 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 60% yield of 4-methylbenzonitrile.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Sources & evidence

ORD record
ord-43c3ba97923a449480474ec5315ed660
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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