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

HRID 480032Notes

Reaction equation

HRID 480032 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 h. After cooling, the reaction mixture was partitioned between CH2Cl2 and H2O and the aqueous phase was further extracted with CH2Cl2. 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 h
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between CH2Cl2 and H2O
  5. extractionthe aqueous phase was further extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-cacdcd702acd45d49095cd387f4aef61
Source dataset
uspto-grants-2003_11
Patent number
US06649620B2

Reaction notes

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