Isovanillin → 3-Hydroxy-4-methoxybenzonitrile

HRID 1072413Notes

Reaction equation

HRID 1072413 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.Cl.[NH2:13]O.[Na+].C([O-])(=O)C>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:13]

Participants

5

Reactant 3

HCID 12127IsovanillinHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 49128223-Hydroxy-4-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

First, a mixture of 3-hydroxy-4-methoxy benzaldehyde (25 g, 164.3 mmol), hydroxylamine hydrochloride (13.7 g, 197.2 mmol), and acetic acid sodium salt (27 g, 328.6 mmol) in acetic acid (200 ml) was refluxed overnight. After cooling, the acetic acid was evaporated under reduced pressure. Water was added to the residue and the resulting precipitate was collected by filtration. The crude product was recrystalized to give 3-hydroxy-4-methoxy benzonitrile. (23.54 g, 96%)

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe acetic acid was evaporated under reduced pressure
  4. additionWater was added to the residue
  5. filtrationthe resulting precipitate was collected by filtration
  6. customThe crude product was recrystalized

Sources & evidence

ORD record
ord-ff5e90962edb4378ad9e46465b10455b
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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