Methanol → 4-Cyanobenzaldehyde

HRID 1385556Notes

Reaction equation

HRID 1385556 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.CO.S(=O)(=O)(O)[OH:24]>C(O)(=O)C.O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:24])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 660424-CyanobenzaldehydeYield 45%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3.9 g of p-cyanobenzylamine, 4.2 g of hexamethylenetetramine, 15 ml of methanol, 15 ml of water and 8 ml of acetic acid were mixed and after adjusting the pH of the solvent to 3 by sulfuric acid, the mixture was reacted at 70° C. for 5 hours while stirring. The reaction solution was concentrated to a half amount in an evaporator and 20 ml of water was added to precipitate crystals. The crystals precipitated were collected by filtration, washed with water and dried to obtain 1.8 g (yield: 45%) of p-cyanobenzaldehyde. The purity was 99.5% or more.

Workup

  1. customthe mixture was reacted at 70° C. for 5 hours
  2. concentrationThe reaction solution was concentrated to a half amount in an evaporator and 20 ml of water
  3. additionwas added
  4. customto precipitate crystals
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d5480f9c33ba4ae194a4235958c060bf
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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