Sodium Iodide → Benzonitrile, 4-[(5-iodopentyl)oxy]-

HRID 6069

Reaction equation

HRID 6069 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[I-:16].[Na+]>CC(C)=O>[I:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Product 1

HCID 16202445Benzonitrile, 4-[(5-iodopentyl)oxy]-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 32.7 g (146 mmol) of 4-(5-chloropentoxy) benzonitrile in 350 mL acetone is added 38.3 g (150 mmol) of sodium iodide in 230 mL of acetone. The reaction is heated to reflux and stirred overnight. The acetone is removed under reduced pressure and the residue partitioned between water and ether. The ethereal layer is dried, filtered and evaporated to give 4-(5-iodopentoxy) benzonitrile, m.p. 51°-54° C.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. customThe acetone is removed under reduced pressure
  4. customthe residue partitioned between water and ether
  5. customThe ethereal layer is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-adbf3dc1a5cb462d9cbba9a96dc56869
Source dataset
uspto-grants-1993_09
Patent number
US05246965

Linked notes

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