Benzaldehyde, 4-(phenylmethoxy)- → 4-Benzyloxy-benzaldehyde oxime

HRID 77737Notes

Reaction equation

HRID 77737 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][OH:18].Cl.C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[N:17][OH:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 7633594-Benzyloxy-benzaldehyde oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

4.24 g of 4-benzyloxy benzaldehyde (20 mmol) was dissolved in a 0.2M mixed solution of ethanol and water (3:1,100 ml), followed by stirring. 2.78 g of NH2OH—HCl (40 mmol) and 2.46 g of sodium acetate(30 mmol) were added thereto, and stirred at room temperature for about 30 minutes. Subsequently, the completion of the reaction was confirmed by liquid chromatography, and water and ethanol were removed by distillation under reduced pressure to obtain a pale yellow solid compound. The pale yellow solid compound was extracted three times with water and ethyl acetate, an organic solvent layer was dried under reduced pressure to obtain a crude product, and the crude product was then purified with a hexane/ethylacetate solution (10:1) to obtain a white solid compound. The obtained solid compound was subjected to subsequent reactions without additional purification.

Workup

  1. stirringstirred at room temperature for about 30 minutes
  2. customwere removed by distillation under reduced pressure
  3. customto obtain a pale yellow solid compound
  4. extractionThe pale yellow solid compound was extracted three times with water and ethyl acetate
  5. customan organic solvent layer was dried under reduced pressure

Sources & evidence

ORD record
ord-3f0ce4815c904f29a068b340a3954c8a
Source dataset
uspto-grants-2014_09
Patent number
US08841335B2

Reaction notes

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