Hydrochloric Acid → (2-chlorobenzyl)(4-chlorophenyl)methanone

HRID 1696181Notes

Reaction equation

HRID 1696181 reaction equation
[Mg].II.[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Cl.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#N)=[CH:16][CH:15]=1.Cl.[O:23]1CCCC1.C(OCC)C>C(OCC)C>[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:18]([C:17]1[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:23]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 119062-Chlorobenzyl chlorideHCID 121634-ChlorobenzonitrileHCID 5462224MagnesiumHCID 21868444Ether tetrahydrofuran

Product 1

HCID 246599(2-chlorobenzyl)(4-chlorophenyl)methanoneYield 74%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To diethylether (250 mL) was added magnesium (6.04 g) and a catalytic amount of iodine, and the mixture was stirred. Thereto was gradually added dropwise 2-chlorobenzyl chloride (20.0 g), and the mixture was stirred for 1 hour from the time when the temperature of such mixture began to rise. Thereto was added a solution of 4-chlorobenzonitrile (18.8 g) in tetrahydrofuran/diethylether (20 mL/50 mL), and the mixture was stirred for 3 hours. To the reaction mixture was added an aqueous 2N hydrochloric acid solution (150 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=40/1 to 20/1) to obtain (2-chlorobenzyl)(4-chlorophenyl)methanone (24.40 g; yield: 74%) as a powder.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=40/1 to 20/1)

Sources & evidence

ORD record
ord-1f77377d25bc4f38b1115a4f13416b86
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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