1,2-Dimethyl-3-nitrobenzene → 1-Methyl-6-nitrophenylacetic acid

HRID 1860903

Reaktionsgleichung

Reaktionsgleichung von HRID 1860903
[C:1]([O:8]CC)(=[O:7])[C:2](OCC)=O.[O-]CC.[K+].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](C)[C:19]=1[CH3:25])([O-:17])=[O:16]>CCOCC>[CH3:25][C:19]1([CH2:2][C:1]([OH:8])=[O:7])[C:18]([N+:15]([O-:17])=[O:16])=[CH:23][CH:22]=[CH:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 67391,2-Dimethyl-3-nitrobenzeneHCID 7268Diethyl OxalateHCID 23670592Potassium ethoxide

Produkt 1

HCID 694190151-Methyl-6-nitrophenylacetic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

Diethyl oxalate (30 mL) in 20 mL of dry ether was added with stirring to 19 g of potassium ethoxide suspended in 50 mL of dry ether. The mixture was cooled in an ice bath and 20 mL of 3-nitro-o-xylene in 20 mL of dry ether was slowly added. The thick dark red mixture was refluxed for 0.5 hr, concentrated, and treated with 10% sodium hydroxide until almost all of the solid dissolved. Hydrogen peroxide (30%) was then added to the dark red mixture until the red color changed to yellow. The mixture was treated alternately with 10% sodium hydroxide and 30% hydrogen peroxide until the dark red color was no longer present. The solid was filtered off and the filtrate acidified with 6 N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with water, and dried under vacuum to give 9.8 g (45% yield) of 1-methyl-6-nitrophenylacetic acid as an off-white solid. The solid was hydrogenated in methanol over 10% palladium on carbon to give 9.04 g of 4-methyl-2-oxindole as a white solid.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. temperatureThe thick dark red mixture was refluxed for 0.5 hr
  3. concentrationconcentrated
  4. additiontreated with 10% sodium hydroxide until almost all of the solid
  5. dissolutiondissolved
  6. additionHydrogen peroxide (30%) was then added to the dark red mixture until the red color
  7. additionThe mixture was treated alternately with 10% sodium hydroxide and 30% hydrogen peroxide until the dark red color
  8. filtrationThe solid was filtered off
  9. filtrationThe resulting precipitate was collected by vacuum filtration
  10. washwashed with water
  11. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-41b04a17b6cc4407b8f1cd5f6e7efaaa
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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