1-Chloro-4-(chloromethyl)benzene → HCID 19789981, compound

HRID 1656022Notes

Reaction equation

HRID 1656022 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:18].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:18][C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[CH:9][C:4]=2[Cl:3])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 19034580HCID 19034580, compound

Product 1

HCID 19789981HCID 19789981, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 0.07 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.40 g of 2-chloro-4-(3-chlorophenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 10 minutes, a solution of 0.25 g of p-chlorobenzyl chloride in 5 ml of N,N-dimethylformamide was added thereto at room temperature, followed by stirring at the same temperature for 10 hours. The reaction mixture was poured into ice-water and extracted twice with 100 ml of ethyl acetate. The extracts were combined together, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 0.48 g of 4-chloro-1-[2-chloro-4-(3-chlorophenoxy)phenoxy]methylbenzene. Yield, 81%. m.p., 72.1° C.

Workup

  1. temperatureice-cooling
  2. customat room temperature
  3. stirringby stirring at the same temperature for 10 hours
  4. extractionextracted twice with 100 ml of ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-638c35dd4e4f499ba2eacab1863be7df
Source dataset
uspto-grants-1993_10
Patent number
US05252610

Reaction notes

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