2-Methoxybenzaldehyde → 5-Chloro-2-methoxybenzaldehyde

HRID 554817Notes

Reaction equation

HRID 554817 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[Cl:11][O-].[Ca+2].Cl[O-]>CC(C)=O.O.C(O)(=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Participants

6

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 24504Calcium hypochlorite

Product 1

HCID 37183565-Chloro-2-methoxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-methoxybenzaldehyde (2g) in acetone (20 ml), water (40 ml) and acetic acid (4 ml) were added. Under ice cooling, calcium hypochlorite (5.25 g) was added, and then the mixture was stirred at that temperature for 1 hour and at room temperature for 2 hours. The reaction solution was extracted with methyl tert-butyl ether (20 ml×2), and the organic layer was washed with an aqueous sodium thiosulfate solution, then dried over magnesium sulfate. The solvent was distilled off in vacuo and the obtained residue was purified by slurry in heptane. The precipitated crystals were collected by filtration and dried in vacuo to obtain the title compound in an amount of 2.2 g as a colorless crystal.

Workup

  1. extractionThe reaction solution was extracted with methyl tert-butyl ether (20 ml×2)
  2. washthe organic layer was washed with an aqueous sodium thiosulfate solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off in vacuo
  5. customthe obtained residue was purified by slurry in heptane
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-116d90120c2b4f2ba9a3c66d3ddc4c83
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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