Sodium Carbonate → Acetic acid, 2-[(3,5,6-trichloro-2-pyridinyl)oxy]-, methyl ester

HRID 1704634

Reaktionsgleichung

Reaktionsgleichung von HRID 1704634
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CO>[Cl:8][C:7]1[C:2]([O:13][CH2:12][C:11]([O:15][CH3:16])=[O:14])=[N:3][C:4]([Cl:10])=[C:5]([Cl:9])[CH:6]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 169902,3,5,6-TetrachloropyridineHCID 66774Methyl Glycolate

Produkt 1

HCID 94596Acetic acid, 2-[(3,5,6-trichloro-2-pyridinyl)oxy]-, methyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A reaction vessel was charged with 43.4 g (0.2 mole) of 2,3,5,6-tetrachloropyridine, 108 g (1.2 mole) of methyl glycolate, and 26.6 g (0.25 mole) of anhydrous sodium carbonate. The resulting mixture was stirred and heated to 110° C. at atmospheric pressure with methanol distillate being removed, as it formed, through a distillation head. After 3.5 hours, 6.5 g of methanol distillate was collected. This distillate, along with 64.0 g of additional methanol was added to the reaction mixture and reflux was continued for 1 hour. The solution was cooled to room temperature and anhydrous hydrogen chloride was sparged in slowly, until the solution was acidic to thereby minimize hydrolysis. The solution was refluxed at 70° C. for two more hours, and volatiles were removed in a vacuum. One hundred and eighteen grams of methanol and methyl glycolate were recovered. Perchloroethylene (150 g) was used to extract the ester. After washing the resulting perchloroethylene solution with water and cooling to 20° C., crystals of the product precipitated. These crystals were filtered and dried to give 41.2 g (0.15 mole) of methyl 3,5,6-trichloro-2-pyridinyloxyacetate, m.p. 99°-103° C. The ester product was analyzed by gas-liquid chromatography and was shown to be about 98% pure. Further recrystallization from methanol gave the pure ester, m.p. 104.5°-106° C. In the filtrate from the original crystallization there was another 8.2 g (0.03 mole) of product, and therefore, the total amount of product was 49.4 g (0.18 mole), which represented a 90% yield based on the tetrachloropyridine.

Aufarbeitung

  1. custombeing removed, as it
  2. customformed, through a distillation head
  3. distillation6.5 g of methanol distillate was collected
  4. additionThis distillate, along with 64.0 g of additional methanol was added to the reaction mixture
  5. temperaturereflux
  6. waitwas continued for 1 hour
  7. customanhydrous hydrogen chloride was sparged in slowly, until the solution
  8. customhydrolysis
  9. temperatureThe solution was refluxed at 70° C. for two more hours, and volatiles
  10. customwere removed in a vacuum
  11. customOne hundred and eighteen grams of methanol and methyl glycolate were recovered
  12. extractionto extract the ester
  13. washAfter washing the resulting perchloroethylene solution with water
  14. temperaturecooling to 20° C.
  15. customcrystals of the product precipitated
  16. filtrationThese crystals were filtered
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2a3f8b8f3743411b8a43d004e451f801
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04127582

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