Sodium Iodide → 3-Acetyl-2,5-bis-(3,3-dichloroprop-2-enyloxy)-1-chlorobenzene

HRID 497043Notes

Reaction equation

HRID 497043 reaction equation
[C:1]([C:4]1[C:5](O)=[C:6]([Cl:11])[CH:7]=[C:8]([OH:10])[CH:9]=1)(=[O:3])[CH3:2].[Cl:13][C:14]([Cl:18])=[CH:15][CH2:16]Cl.[C:19](=[O:22])([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[C:1]([C:4]1[C:5]([O:22][CH2:19][CH:15]=[C:14]([Cl:18])[Cl:13])=[C:6]([Cl:11])[CH:7]=[C:8]([O:10][CH2:16][CH:15]=[C:14]([Cl:18])[Cl:13])[CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 223186121-(3-Chloro-2,5-dihydroxyphenyl)ethanone

Product 1

HCID 223186103-Acetyl-2,5-bis-(3,3-dichloroprop-2-enyloxy)-1-chlorobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.9 g of 3-acetyl-1-chloro-2,5-dihydroxybenzene were dissolved in 29 ml of acetone, and 3.39 g of 1,1,3-trichloropropene, 4.3 g of potassium carbonate and 0.7 g of sodium iodide were added. The mixture was heated under reflux for 5 hours (monitored by TLC). The reaction mixture was then allowed to cool and concentrated using a rotary evaporator, and the resulting crude product was subjected to chromatographic purification. Yield: 6.1 g (99%)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours (monitored by TLC)
  3. temperatureto cool
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customthe resulting crude product was subjected to chromatographic purification

Sources & evidence

ORD record
ord-507b5d5a7bc2439ebb7d816ff589ddb9
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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