Dimethylformamide → 2-(3-Chlorophenoxymethyl)-alpha-methoxyiminobenzyl chloride

HRID 279442Notes

Reaction equation

HRID 279442 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([Cl:28])=[N:25][O:26][CH3:27]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([Cl:28])=[N:25][O:26][CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 539269502-Chloromethyl-alpha-methoxyiminobenzyl chloride

Product 1

HCID 544326462-(3-Chlorophenoxymethyl)-alpha-methoxyiminobenzyl chlorideYield 91.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Chlorophenol (3.09 g, 0.024 mol), dimethyl-formamide (20 ml) and potassium carbonate (4.15 g, 0.03 mol) were added to 2-chloromethyl-α-methoxyiminobenzyl chloride (4.36 g, 0.02 mol), and the mixture was stirred at room temperature for 4 days. After completion of the reaction, ether (250 ml) was added, and the mixture was washed with brine (200 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl chloride (5.66 g, 91.2%) as a colorless oil.

Workup

  1. additionwas added
  2. washthe mixture was washed with brine (200 ml) twice
  3. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-7dc6e06ddcfa44dfaaa13a2a28d3a7de
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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