Hydroxyamine hydrochloride → 2-Butyl-benzofuran-3-carbaldehyde oxime

HRID 735883Notes

Reaction equation

HRID 735883 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH:10]=O)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[Na+].Cl.[NH2:22][OH:23]>CO.O>[CH2:1]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH:10]=[N:22][OH:23])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 49619662-Butyl-1-benzofuran-3-carbaldehyde

Product 1

HCID 858544212-Butyl-benzofuran-3-carbaldehyde oximeYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 2-butyl-1-benzofuran-3-carbaldehyde (25 g, 0.124 mol) and sodium acetate (12.2 g, 0.124 mol) in methanol (100 mL) was added hydroxylamine hydrochloride (10.3 g, 0.149 mol) in water (25 mL) at 0° C. The mixture was stirred at rt for 2 h. Water (300 mL) was added to the reaction mixture and the product was extracted with EtOAc. The organic layer was dried and concentrated under vacuum to give crude 2-butyl-1-benzofuran-3-carbaldehyde oxime (25 g, 93%) as a light brown liquid.

Workup

  1. extractionthe product was extracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-72f836848f06431baa7f625307009422
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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