Water → 4-Cyanobenzaldehyde

HRID 1385552Notes

Reaction equation

HRID 1385552 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.S(=O)(=O)(O)[OH:23]>C(O)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:23])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 660424-CyanobenzaldehydeYield 78.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

56.2 g of p-cyanobenzylamine, 59.6 g of hexamethylenetetramine, 46 ml of water, 320 ml of acetic acid and 46.0 g of 98% sulfuric acid were mixed and reacted at 100° C. for 2 hours while stirring. The reaction solution was concentrated to about a half amount in an evaporator and 400 ml of water was added to precipitate crystals. The crystals precipitated were collected by filtration, washed with water and dried to obtain 43.8 g (yield: 78%) of p-cyanobenzaldehyde. The purity was 99.8% or more.

Workup

  1. customreacted at 100° C. for 2 hours
  2. concentrationThe reaction solution was concentrated to about a half amount in an evaporator and 400 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-c98bdfcd1a56434a9011f6ef637931c3
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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