Water → 4-Cyanobenzaldehyde

HRID 1385564Notes

Reaction equation

HRID 1385564 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]N)=[CH:5][CH:4]=1)#[N:2].S(OOS([O-])(=O)=O)([O-])(=O)=[O:12].[Na+].[Na+].O>CO>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 62655Sodium PersulfateHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 660424-CyanobenzaldehydeYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.2 g of p-cyanobenzylamine, 28.6 g of sodium persulfate, 10 ml of water, and 100 ml of methanol were mixed and allowed to react at 50° C. for 40 minutes while stirring. After cooling the reaction mixture to room temperature, methanol was distilled off to precipitate solids. To the resulting suspension was added dichloromethane for extraction. The organic layer was washed twice with saturated aqueous sodium bicarbonate solution and then twice with water, and then magnesium sulfate was added thereto. The residue after distilling off dichloromethane was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=5/1), and hexane and ethyl acetate were distilled off. The resultant crude product concentrated to dryness was recrystallized from cyclohexane, the crystals were filtered, and dried to obtain 7.7 g (yield: 58%) of p-cyanobenzaldehyde. The obtained p-cyanobenzaldehyde had a purity of 99% by the analysis of high performance liquid chromatography.

Workup

  1. customto react at 50° C. for 40 minutes
  2. distillationmethanol was distilled off
  3. customto precipitate solids
  4. additionTo the resulting suspension was added dichloromethane
  5. extractionfor extraction
  6. washThe organic layer was washed twice with saturated aqueous sodium bicarbonate solution
  7. additiontwice with water, and then magnesium sulfate was added
  8. distillationThe residue after distilling off dichloromethane
  9. distillationwere distilled off
  10. concentrationThe resultant crude product concentrated to dryness
  11. customwas recrystallized from cyclohexane
  12. filtrationthe crystals were filtered
  13. customdried

Sources & evidence

ORD record
ord-7e646b1f8a564728b3686e9a0377ad56
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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