4-(Chloromethyl)benzaldehyde → 4-Chloromethylbenzaldehyde oxime

HRID 81374Notes

Reaction equation

HRID 81374 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1>CCO>[Cl:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[N:2][OH:3])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3578774-(Chloromethyl)benzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 762257374-Chloromethylbenzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydroxylamine hydrochloride (10.11 g, 145.5 mmol) was added to a solution of 4-(chloromethyl)benzaldehyde 4 (7.5 g, 48.51 mmol) in EtOH. The mixture was heated at 50° C. for 3 h then concentrated in vacuo. The residue was partitioned between DCM and water. The combined organic extract was dried (MgSO4) and concentrated in vacuo yielding a white solid that was used without further purification (8.1 g, 98%). 1H NMR (400 MHz, DMSO) δ 4.77 (2H, s), 7.46 (2H, d, J=8.0 Hz), 7.60 (2H, d, J=8.0 Hz), 8.15 (1H, s), 11.32 (1H, s).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. extractionThe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customyielding a white solid that
  7. customwas used without further purification (8.1 g, 98%)

Sources & evidence

ORD record
ord-bf4792e1c3eb4877a155312d7bb2384b
Source dataset
uspto-grants-2014_09
Patent number
US08846686B2

Reaction notes

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