Formaldehyde → 4-Cyanobenzaldehyde

HRID 1385557Notes

Reaction equation

HRID 1385557 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]N)=[CH:5][CH:4]=1)#[N:2].C=O.C([O-])(=[O:15])C.[NH4+].O>C(O)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:15])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 826084-(Aminomethyl)benzonitrileHCID 517165Ammonium Acetate

Product 1

HCID 660424-CyanobenzaldehydeYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

13.2 g of p-cyanobenzylamine, 12.0 g of paraformaldehyde, 46.0 g of ammonium acetate, 60 ml of water and 60 ml of acetic acid were mixed and reacted at 100° C. for 3 hours while stirring. The reaction solution was concentrated to a half amount in an evaporator and water in an amount equal to the amount of solvent distilled off was added to precipitate crystals. The crystals precipitated were collected by filtration, washed with water and dried to obtain 8.0 g (yield: 62%) of p-cyanobenzaldehyde. The purity was 99.5% or more.

Workup

  1. customreacted at 100° C. for 3 hours
  2. concentrationThe reaction solution was concentrated to a half amount in an evaporator and water in an amount equal to the amount of solvent
  3. distillationdistilled off
  4. additionwas added
  5. customto precipitate crystals
  6. customThe crystals precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-ad0c2f9bc1e84ad1b6c15e46daf56311
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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