4-Chlorophenol → HCID 726068, compound

HRID 1862793Notes

Reaction equation

HRID 1862793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20].[OH-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([F:20])([F:21])[F:22])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 726068HCID 726068, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution containing 64.2 g (0.5 mole) of 4-chlorophenol and 112.7 g (0.5 mole) of 2-chloro-5-nitrobenzotrifluoride in 400 ml of DMSO was added dropwise with stirring at 30°-35° C. a solution containing 20 g (0.5 mole) of sodium hydroxide in 20 ml of water. After 1.5 hours, the reaction mixture was poured into cold water and extracted with 800 ml of ether. The ether solution was dried and concentrated under reduced pressure to give 158 g (99%) of product that crystallized on standing; melting point, 46°-48° C. (from hexane).

Workup

  1. additionwas added dropwise
  2. extractionextracted with 800 ml of ether
  3. dry with materialThe ether solution was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e85876a87a644b3da1f65a7562cc3286
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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