Ethylene Glycol → (4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

HRID 83795

Reaktionsgleichung

Reaktionsgleichung von HRID 83795
Cl.[N+:2]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:16](O)[CH2:17][OH:18]>>[OH:18][CH2:17][CH2:16][O:12][C:11](=[O:13])[CH2:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:15][CH:14]=1

Komponenten

4

Edukt 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 15720(4-Nitrophenoxy)acetic acid

Produkt 1

HCID 59253945(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl esterAusbeute 57,4 %

Versuchsvorschrift

Dry HCl gas was passed through a mixture of (4-nitrophenoxy)acetic acid 22 (100 g, 507 mmol) and ethylene glycol (300 ml) for 1 hour. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (2 kg). Crude 23 was filtered, dried and purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to give pure 23 (70 g, 57.4%) as a white powder with an m.p. between 73.5-75.5° C.

Aufarbeitung

  1. customDuring HCl gas bubbling the temperature
  2. customrose to 60° C
  3. customThe crude reaction mass
  4. additionwas poured onto ice (2 kg)
  5. filtrationCrude 23 was filtered
  6. customdried
  7. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1c5655145141470a8899330a915486d4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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