2,4-Dichlorobenzyl chloride → HCID 13232345, compound

HRID 358074Notes

Reaction equation

HRID 358074 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[Mg].[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O.[Cl-].[NH4+]>C(OCC)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[C:13](/[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)\[CH3:12]

Participants

6

Reactant 4

HCID 72122,4-Dichlorobenzyl chlorideHCID 7467P-ChloroacetophenoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 13232345HCID 13232345, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

118 g of 2,4-dichlorobenzyl chloride were added dropwise to 14.6 g of magnesium turnings in 400 ml of dry diethyl ether at the boiling point. After the reaction was complete, a solution of 77.3 g of 4-chloroacetophenone in 400 ml of dry diethyl ether was added. Thereafter, decomposition was effected with aqueous ammonium chloride solution, the organic phase was separated off, washed neutral, dried over sodium sulfate and evaporated down under reduced pressure, the residue was taken up in 1 liter of toluene and the solution was refluxed with 4 g of 4-methylbenzenesulfonic acid, in a water separator. After dehydration was compelete, the toluene phase was washed with sodium carbonate solution and water and dried over sodium sulfate, the solvent was evaproated off and the residue was recrystallized from methanol to give 107 g (81.9%) of E-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)-prop-1-ene of melting point 84°-85° C.

Workup

  1. customthe organic phase was separated off
  2. washwashed neutral
  3. dry with materialdried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. temperaturethe solution was refluxed with 4 g of 4-methylbenzenesulfonic acid, in a water separator
  6. washthe toluene phase was washed with sodium carbonate solution and water
  7. dry with materialdried over sodium sulfate
  8. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-6fcc61761d5b4f8d868a7c800939249a
Source dataset
uspto-grants-1984_08
Patent number
US04464381

Reaction notes

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