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

HRID 37322

Reaction equation

HRID 37322 reaction equation
[CH3:1][C:2]1[C:7]([Cl:8])=[C:6](Cl)[C:5]([CH3:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[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:6]1[C:5]([CH3:10])=[CH:4][C:3]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[C:7]=1[Cl:8]

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

Into a round bottom reaction flask equipped with a magnetic stirrer, condenser, thermometer and nitrogen inlet was added 50.0 grams (0.23 mol) of 2,5-dimethyl-3,4-dichloronitrobenzene, 38.5 grams (0.32 mol) of 2,4-dimethylphenol, 50 grams (0.36 mol) of potassium carbonate and 125 milliliters of dimethylformamide. The reaction mixture was heated to a temperature of 90° C.-100° C. and maintained at this temperature for a period of 72 hours. The reaction mixture was then cooled, filtered and concentrated to give a dark oil. The dark oil was partitioned between toluene (300 milliliters) and 4% sodium hydroxide (250 milliliters) and then separated. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated to give a dark oil. The dark oil was trituated with hexane and a solid was formed. The solid was washed with cold hexane and vacuum dried to give 47.8 grams (0.16 mol) of 4-(2,4-dimethylphenoxy) 2,5-dimethyl-3-chloronitrobenzene as a tan powder having a melting point of 78° C.-80° C. Elemental analysis of the tan powder indicated the following:

Workup

  1. customInto a round bottom reaction flask equipped with a magnetic stirrer, condenser
  2. temperatureThe reaction mixture was heated to a temperature of 90° C.-100° C.
  3. temperaturemaintained at this temperature for a period of 72 hours
  4. temperatureThe reaction mixture was then cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark oil
  8. customThe dark oil was partitioned between toluene (300 milliliters) and 4% sodium hydroxide (250 milliliters)
  9. customseparated
  10. washThe organic layer was washed with water and brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated
  13. customto give a dark oil
  14. customa solid was formed
  15. washThe solid was washed with cold hexane and vacuum
  16. customdried

Sources & evidence

ORD record
ord-403b3b6d780f4d52ba8ef616caf6a946
Source dataset
uspto-grants-1995_05
Patent number
US05420163

Linked notes

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