Dimethyl Sulfoxide → 1-(3-Methoxyphenoxy)-2-nitrobenzene

HRID 1609258Notes

Reaction equation

HRID 1609258 reaction equation
CS(C)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[OH-].[K+].Cl[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]>O>[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:13][C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[CH:11][CH:10]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69451-Chloro-2-nitrobenzeneHCID 90073-MethoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 93111371-(3-Methoxyphenoxy)-2-nitrobenzeneYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 150 ml of dimethyl sulfoxide were added 19.9 g of 3-methoxyphenol and 9.1 g of potassium hydroxide and the mixture was heated to 70°-80° C. to prepare a homogeneous solution. To this solution was added 21.1 g of 2-chloronitrobenzene and the mixture was stirred at 100° C. for 4 hours. The reaction mixture was then diluted with water and extracted with ether and the ether extract was washed succesively with 10% sodium hydroxide solution and saturated sodium chloride solution. The washed extract was dried over magnesium sulfate and the ether was distilled off to give 31.9 g of the title compound as a light yellow solid.

Workup

  1. temperaturethe mixture was heated to 70°-80° C.
  2. customto prepare a homogeneous solution
  3. extractionextracted with ether
  4. extractionthe ether extract
  5. washwas washed succesively with 10% sodium hydroxide solution and saturated sodium chloride solution
  6. extractionThe washed extract
  7. dry with materialwas dried over magnesium sulfate
  8. distillationthe ether was distilled off

Sources & evidence

ORD record
ord-500c6b71d7d246e6b7fcefc9a857dc8f
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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