4-(Chloromethyl)benzaldehyde → 4-Chloromethylbenzaldehyde oxime
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- concentrationthen concentrated in vacuo
- customThe residue was partitioned between DCM and water
- extractionThe combined organic extract
- dry with materialwas dried (MgSO4)
- concentrationconcentrated in vacuo
- customyielding a white solid that
- 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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