3-Benzyloxy-4-methoxybenzaldehyde → 3-(Benzyloxy)-4-methoxybenzonitrile

HRID 2228485Notes

Reaction equation

HRID 2228485 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:25]O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:12]#[N:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 27522763-(Benzyloxy)-4-methoxybenzonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Benzyloxy-4-methoxybenzaldehyde (50 g, 0.21 mol) was added to a solution of sodium acetate (33.9 g, 0.41 mol) and hydroxylamine hydrochloride (28.73 g, 0.41 mol) in acetic acid (200 ml) and the resulting suspension was heated to reflux for 18 hours. After cooling, the reaction mixture was partitioned between dichloromethane and water and the aqueous phase was further extracted with dichloromethane. The combined organic layers were dried over MgSO4 and evaporated to afford the subtitle compound as a buff-coloured solid (43.9 g, 89%). Rf 0.70 (toluene:EtOAc 4:1, v/v).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between dichloromethane and water
  5. extractionthe aqueous phase was further extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-ca860ad41c374bcaaffda13cde8f5766
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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