Ethyl Acetate → N-[(3,5-Dimethylphenyl)methylidene]hydroxylamine

HRID 339451

Reaction equation

HRID 339451 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.C([O-])(=O)C.[Na+].Cl.[NH2:17][OH:18].C(OCC)(=O)C>CO.CCCCCC.O.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=[N:17][OH:18]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 34225Benzaldehyde, 3,5-dimethyl-HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 71401900N-[(3,5-Dimethylphenyl)methylidene]hydroxylamine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A 2 L round bottom flask was set up with a mechanical stirrer, thermometer, N2 inlet and reflux condensor. A solution of 3,5-dimethyl-benzaldehyde (70 g. 522 mmol) in 300 mL of methanol was added, followed by the addition of sodium acetate (44 g, 536 mmol). Hydroxylamine-HCl (37 g, 532 mmol) was added portion-wise over 5 minutes, during which time the maximum temperature reached without cooling was 27° C. The mixture was stirred for an additional 2 hours at room temperature. TLC (10% ethyl acetate in hexane) indicated the absence of the starting aldehyde and the appearance of oxime. Most of the methanol was removed on a rotary evaporator, resulting in the formation of a precipitate. Ether and water were added to the concentrated suspension, and then the ether layer was collected, dried over MgSO4, and removed on a rotary evaporator. The white crystalline material was air-dried, resulting in 77 g (100%) of 3,5-dimethyl-benzaldehyde oxime. 1H-NMR (300 MHz, CDCl3) δ (ppm): 8.09 (s, 1H), 7.22 (s, 2H), 7.05 (s, 1H), 2.33 (s, 6H).

Workup

  1. customA 2 L round bottom flask was set up with a mechanical stirrer
  2. temperaturethermometer, N2 inlet and reflux condensor
  3. temperaturewithout cooling
  4. customwas 27° C
  5. customMost of the methanol was removed on a rotary evaporator
  6. customresulting in the formation of a precipitate
  7. customthe ether layer was collected
  8. dry with materialdried over MgSO4
  9. customremoved on a rotary evaporator
  10. customThe white crystalline material was air-dried
  11. customresulting in 77 g (100%) of 3,5-dimethyl-benzaldehyde oxime

Sources & evidence

ORD record
ord-b34b8717899144d7ba1e5eedffb7a0cf
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Linked notes

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