Dicyclohexylcarbodiimide → (4-Nitrophenoxy)-acetic acid-2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester

HRID 83796

Reaktionsgleichung

Reaktionsgleichung von HRID 83796
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O[CH2:16][CH2:17][O:18][C:19](=[O:31])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH2:16][CH2:17][O:18][C:19](=[O:31])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:11])=[CH:13][CH:14]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 15720(4-Nitrophenoxy)acetic acidHCID 59253945(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

Produkt 1

HCID 59253942(4-Nitrophenoxy)-acetic acid-2-[2-(4-nitrophenoxy)-acetoxy]-ethyl esterAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of (4-nitrophenoxy)acetic acid 22 (80 g, 406 mmol) and (4-nitrophen-oxy)-acetic acid-2-hydroxyethyl ester 23 (80 g, 332 mmol) in anhydrous dichloro-methane (2 L) under nitrogen atmosphere was added a solution of 1,3-di-cyclohexyl carbodiimide (128 g, 620 mmol) in anhydrous dichloromethane (750 ml) drop wise. The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 24. The crude 24 was purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to get pure 24 (75 grams, 54%) as a white powder with an m.p. between 138-139° C.

Aufarbeitung

  1. filtrationThe solids were filtered off
  2. distillationdichloromethane distilled off
  3. customto get crude 24
  4. customThe crude 24 was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-486a705b4382419baec75d8a649cccc6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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