Dimethylformamide → 3-Chloro-2-(2,4-dimethylphenoxy)-1,4-dimethyl-5-nitrobenzene

HRID 2351466Notes

Reaction equation

HRID 2351466 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[C:5]([CH3:10])=[C:6]([Cl:9])[C:7]=1Cl.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCCCCC>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[O:22][C:7]1[C:6]([Cl:9])=[C:5]([CH3:10])[C:4]([N+:11]([O-:13])=[O:12])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77712,4-DimethylphenolHCID 11430Potassium CarbonateHCID 137729272,3-Dichloro-1,4-dimethyl-5-nitrobenzene

Product 1

HCID 148206053-Chloro-2-(2,4-dimethylphenoxy)-1,4-dimethyl-5-nitrobenzeneYield 69.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a flask equipped with condenser, stirrer, under nitrogen, was added 3,6-dimethyl-4,5-dichloronitrobenzene (50 g, 0.23 mol), 2,4-dimethylphenol (38.5 g, 0.32 mol), potassium carbonate (50 g, 0.36 mol), and dimethylformamide (125 ml). The resulting mixture was heated at 90°~100° for 72 hours. It was then cooled, filtered, and concentrated to give dark oil. It was partitioned between toluene (300 ml) and 4% sodium hydroxide (250 ml) and then separated. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated to give dark oil. Solid was formed after the oil was trituated with hexane. The solid was washed with cold hexane and vacuum dried to give a tan powder (47.8 g, 0.16 mol); mp 78°~80°.

Workup

  1. customTo a flask equipped with condenser, stirrer, under nitrogen
  2. temperatureThe resulting mixture was heated at 90°~100° for 72 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give dark oil
  7. customIt was partitioned between toluene (300 ml) and 4% sodium hydroxide (250 ml)
  8. customseparated
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customto give dark oil
  13. customSolid was formed after the oil
  14. washThe solid was washed with cold hexane and vacuum
  15. customdried

Sources & evidence

ORD record
ord-9acff3391cf54620b021d0c8e3b68ee7
Source dataset
uspto-grants-1989_10
Patent number
US04873264

Reaction notes

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