1,2,3-Trichlorobenzene → 2,3-Dichloroanisole

HRID 1438909Notes

Reaction equation

HRID 1438909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[Cl:9].[CH3:10][O-:11].[Na+]>CC(N(C)C)=O.CO.O>[Cl:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[O:11][CH3:10]

Participants

6

Reactant 2

HCID 68951,2,3-TrichlorobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 161262,3-Dichloroanisole

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

363 g (1 mole) of 1,2,3-trichlorobenzene is dissolved in 600 ml dimethyl acetamide and heated to 125° with stirring. 500 ml of 25% commercial sodium methoxide in methanol is then added at such a rate that the temperature is maintained at 125°-130°. After addition is complete the temperature is maintained at 130° for 30 minutes. The mixture is diluted with water and extracted with toluene. The toluene extracts are washed with brine, dried and the toluene removed by distillation. The residue is fractionated to yield 200 g of the desired isomer 2,3-dichloroanisole bp 140°/29 mm. By appropriate fractionation the minor isomer 2,3-dichloroanisole may also be obtained.

Workup

  1. temperatureheated to 125°
  2. temperatureis maintained at 125°-130°
  3. additionAfter addition
  4. temperatureis maintained at 130° for 30 minutes
  5. extractionextracted with toluene
  6. washThe toluene extracts are washed with brine
  7. customdried
  8. customthe toluene removed by distillation

Sources & evidence

ORD record
ord-089d48eb433546c89d1b64a3e8868b48
Source dataset
uspto-grants-1977_11
Patent number
US04057585

Reaction notes

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