4-Chloro-2-nitrophenol → HCID 361282, compound

HRID 1198525Notes

Reaction equation

HRID 1198525 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.O>[CH2:14]([O:10][C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 69804-Chloro-2-nitrophenolHCID 7503Benzyl ChlorideHCID 24758Sodium hydride

Product 1

HCID 361282HCID 361282, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride dispersion in oil (4.4 g, 0.11 mol) was added in portions over 15 minutes to a stirred solution of 4-chloro-2-nitrophenol (17.4 g, 0.10 mol) in dimethylformamide (200 ml) at 0°-5° C. The mixture was stirred for 15 minutes then benzyl chloride (12.7 g, 0.10 mol) was added dropwise over 5 minutes. The mixture was stirred for 5 days at room temperature, diluted with water and extracted with ether. The extract was washed three times with water, dried and evaporated and the residue was triturated with petroleum spirit.

Workup

  1. stirringThe mixture was stirred for 5 days at room temperature
  2. extractionextracted with ether
  3. washThe extract was washed three times with water
  4. customdried
  5. customevaporated
  6. customthe residue was triturated with petroleum spirit

Sources & evidence

ORD record
ord-481208d31aee4bfa8c9ebdb55502c942
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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