Sodium Cyanide → 4-Propylbenzeneacetonitrile

HRID 2405651Notes

Reaction equation

HRID 2405651 reaction equation
I[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH3:11])=[CH:5][CH:4]=1.[C-:12]#[N:13].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CN(C)C=O>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:12]#[N:13])=[CH:4][CH:5]=1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 86690145HCID 86690145, compound

Product 1

HCID 195934794-PropylbenzeneacetonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon condition, 1-(iodomethyl)-4-propylbenzene (73.6 mg, 0.283 mmol) was dissolved in 1 mL of well-dried N,N-dimethylformamide (dry DMF) and then sodium cyanide (NaCN; 27.7 mg, 0.566 mmol) was added and the reaction mixture was stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 3 mL of water and the mixture was extracted with diethyl ether (3 mL×3). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 41.0 mg (0.257 mmol, 91%) of the desired compound.

Workup

  1. customUpon completion of the reaction
  2. customthe reaction was terminated
  3. additionby adding 3 mL of water
  4. extractionthe mixture was extracted with diethyl ether (3 mL×3)
  5. customThe organic layer thus obtained
  6. customto remove water
  7. filtrationThe precipitate was filtered out
  8. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-f1e853900e3840b6907a68a836cc79a4
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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