Sulfuric Acid → 4-Cyanobenzaldehyde

HRID 1385558Notes

Reaction equation

HRID 1385558 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:12]COC.C(=O)([O-])[O-].[NH4+].[NH4+].S(=O)(=O)(O)O>O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8020DimethoxymethaneHCID 826084-(Aminomethyl)benzonitrileHCID 517111Ammonium Carbonate

Product 1

HCID 660424-CyanobenzaldehydeYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

13.2 g of p-cyanobenzylamine, 30.0 g of formaldehyde dimethyl acetal, 38.4 g of ammonium carbonate and 80 ml of water were reacted after adjusting the pH of the solvent to 2.5 by sulfuric acid, at 90° C. for 4 hours while stirring. The reaction solution was cooled to room temperature and then cooled on ice. The crystals precipitated were collected by filtration, washed with water and dried to obtain 5.1 g (yield: 39%) of p-cyanobenzaldehyde. The purity was 99.5% or more.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. temperaturecooled on ice
  3. customThe crystals precipitated
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d3123729a73a4e448e0967e0679c883c
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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