Water → 2,3-Dimethyl-4-nitrobenzonitrile

HRID 1269861Notes

Reaction equation

HRID 1269861 reaction equation
[C-:1]#[N:2].[K+].FC(F)(F)S(O[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([CH3:19])[C:11]=1[CH3:20])(=O)=O.S([O-])(O)(=O)=O.[K+].O>O1CCCC1>[CH3:20][C:11]1[C:12]([CH3:19])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[C:1]#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 516920Potassium bisulfateHCID 229333962,3-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 229337662,3-Dimethyl-4-nitrobenzonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium cyanide (2.26 g, 34.7 mmol) was added to a solution of 2,3-dimethyl-4-nitrophenyl trifluoromethane-sulfonate (5.20 g, 17.4 mmol) in tetrahydrofuran (21 ml) at room temperature, followed by deaeration. After tetrakistriphenylphosphine (1.00 g, 0.865 mmol) was added thereto, deaeration was conducted again and then the reaction was carried out under reflux conditions for 10 hours. A 0.5M-aqueous potassium hydrogensulfate solution and then water were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and distilled to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform) to obtain 2,3-dimethyl-4-nitrobenzonitrile (2.79 g, 90.9%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform)

Sources & evidence

ORD record
ord-6ad78ac1ef414eb8af15acd0876d046d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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