4-Methylbenzyl chloride → HCID 19792250, compound

HRID 1655438Notes

Reaction equation

HRID 1655438 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:19].[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>CN(C)C=O>[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:19][C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=3)=[CH:9][C:4]=2[Cl:3])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 77224-Methylbenzyl chlorideHCID 24758Sodium hydrideHCID 19792251HCID 19792251, compound

Product 1

HCID 19792250HCID 19792250, compoundYield 81.7%

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 0.45 g of 2-chloro-4-(3,4-dichlorophenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.22 g of p-methylbenzylchloride 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 0.50 g of 4-methyl-1-[2-chloro-4-(3,4-dichlorophenoxy)phenoxy]methylbenzene. Yield, 81%. nD27 :1.6029

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-2dbc8940d5ca4fcd89d3c5d6ca2ff24a
Source dataset
uspto-grants-1993_10
Patent number
US05250574

Reaction notes

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