Sodium Hydroxide → 4-Benzyloxy-3-methoxy-benzonitrile

HRID 749150Notes

Reaction equation

HRID 749150 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:25]O.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:25])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 7937714-Benzyloxy-3-methoxy-benzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-benzyloxy-3-methoxybenzaldehyde (157 g, 649 mmol), sodium acetate (106 g, 1.29 mol), hydroxylamine hydrochloride (90 g, 1.29 mol) and acetic acid (500 ml) was heated at reflux for 21 hours. The solvent was evaporated and ice/water (1000 ml) was added to the residue forming a sticky solid. The mixture was neutralised with aqueous sodium hydroxide solution then extracted with dichloromethane (2×500 ml). The organic solution was washed with 1.0 N sodium hydroxide (100 ml), brine (100 ml) and then dried over magnesium sulphate. Solvent evaporation in vacuo, trituration of the residue with hexane:ethyl acetate (3:1) and collection of the solid by suction filtration yielded 4-benzyloxy-3-methoxybenzonitrile (123 g, 80% yield) as a brown solid:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours
  3. customThe solvent was evaporated
  4. additionice/water (1000 ml) was added to the residue
  5. customforming a sticky solid
  6. extractionthen extracted with dichloromethane (2×500 ml)
  7. washThe organic solution was washed with 1.0 N sodium hydroxide (100 ml), brine (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customSolvent evaporation in vacuo, trituration of the residue
  10. customwith hexane:ethyl acetate (3:1) and collection of the solid
  11. filtrationby suction filtration

Sources & evidence

ORD record
ord-f2169665e72345cc96a1340fd320e72d
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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