Water → Methyl 4-(hydroxyiminomethyl)benzoate

HRID 1386602Notes

Reaction equation

HRID 1386602 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH:1]=[N:14][OH:15])=[CH:4][CH:5]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 6804457Methyl 4-(hydroxyiminomethyl)benzoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl 4-formylbenzoate (4.92 g), hydroxylamine hydrochloride (5.21 g) and sodium acetate (6.15 g) in ethanol (50 ml) was refluxed for 2 hours. The mixture was poured into water and extracted with ethyl acetate and the separated organic layer was washed with brine and dried over magnesium sulfate. The solvents were removed under reduced pressure to give 4-methoxycarbonyl-benzaldehyde oxime (5.28 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washthe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-2da2f43ac0da40d6ae843f0ad679961e
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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