Ethanol → 2,4,6-Trichlorophenoxyacetic acid

HRID 652412

Reaktionsgleichung

Reaktionsgleichung von HRID 652412
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].C(O)C.C[O-].[Na+].Br[CH2:18][C:19]([OH:21])=[O:20]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH2:18][C:19]([OH:21])=[O:20]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 6227Bromoacetic Acid2×HCID 69142,4,6-TrichlorophenolHCID 10942334Sodium Methoxide2×

Produkt 1

HCID 113312,4,6-Trichlorophenoxyacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

2,4,6-trichlorophenol, 100.7 gm, was added to 250 ml of ethanol. 228.6 ml of a 25% solution of sodium methoxide (2 equivalents) in methanol was then added to the system. The system was stirred at room temperature for approximately 1 hour. Afterwards, 69.5 gm of bromoacetic acid was added and the system was then heated to reflux. After 18 hours, an additional equivalent of sodium methoxide in methanol (114.3 ml) was added as well as 34.7 gm of bromoacetic acid. The system was continued at reflux for 12 hours. The reaction was then stopped and the solvent removed by stripping. The resulting solid was washed with water and then with ether. Concentrated HCl was next added to the solid precipitate and the system was left standing for 12 hours. Afterwards, the product was filtered, washed with water and air dried. Toluene was then added to the product. The toluene was removed by stripping and any remaining water was azeotroped off with the toluene. 74.4 gm of 2,4,6-trichlorophenoxyacetic acid was recovered.

Aufarbeitung

  1. temperaturethe system was then heated to reflux
  2. waitAfter 18 hours
  3. temperatureat reflux for 12 hours
  4. customthe solvent removed by stripping
  5. washThe resulting solid was washed with water
  6. additionConcentrated HCl was next added to the solid precipitate
  7. waitthe system was left
  8. waitstanding for 12 hours
  9. filtrationAfterwards, the product was filtered
  10. washwashed with water and air
  11. customdried
  12. additionToluene was then added to the product
  13. customThe toluene was removed
  14. customany remaining water was azeotroped off with the toluene
  15. custom74.4 gm of 2,4,6-trichlorophenoxyacetic acid was recovered

Quellen und Nachweise

ORD-Eintrag
ord-490ceb5379444035a2aebb91a77fc777
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04672065

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