Acetic Acid → 4-Cyanobenzaldehyde

HRID 1385555Notes

Reaction equation

HRID 1385555 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]N)=[CH:5][CH:4]=1)#[N:2].C1N2CN3CN(C2)CN1C3.O.C(O)(=[O:24])C>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:24])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4101HexamethylenetetramineHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 660424-CyanobenzaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.9 g of p-cyanobenzylamine, 8.4 g of hexamethylenetetramine, 40 ml of water, 20 ml of acetic acid and 50 ml of toluene were mixed and reacted at 90° C. for 2 hours while stirring. The reaction solution was cooled to room temperature and the toluene layer was separated, washed with water and concentrated until crystals were precipitated. The concentrated toluene solvent was placed in water, the toluene was removed by azeotropic distillation, and the residue was cooled to room temperature. The crystals precipitated were collected by filtration, washed with water and dried to obtain 4.8 g (yield: 60%) of p-cyanobenzaldehyde. The purity was 99.5% or more.

Workup

  1. customreacted at 90° C. for 2 hours
  2. customthe toluene layer was separated
  3. washwashed with water
  4. concentrationconcentrated until crystals
  5. customwere precipitated
  6. customthe toluene was removed by azeotropic distillation
  7. temperaturethe residue was cooled to room temperature
  8. customThe crystals precipitated
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-07531a4b9ccf4750b6836ba5342d02ba
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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