3-Nitrophenol → 4-(4-Nitrophenoxymethyl)-2-methoxycarbonyl-furan

HRID 71347

Reaktionsgleichung

Reaktionsgleichung von HRID 71347
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC[C:13]1[O:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:14]=1.[C:22]([O-])([O-])=[O:23].[K+].[K+]>CC(C)=O.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:23][CH2:22][C:14]2[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[O:17][CH:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoate

Produkt 1

HCID 220610744-(4-Nitrophenoxymethyl)-2-methoxycarbonyl-furanAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3-Nitrophenol (1.0 g, 7.19 mmole), methyl 5-(chloromethyl)-2-furoate (1.38 g, 7.90 mmole) and anhydrous K2CO3 (1.19 g, 8.60 mmole) in acetone (30 mL) were refluxed for 8 h. The reaction mixture was cooled and diluted with water. The resultant white solid was filtered, washed with water and air dried overnight to give 1.81 g (90%) of the desired product. 1H NMR (CDCl3): δ 7.86 (dd, 1H, J=2.3 and 8.2 Hz), 7.80 (t, 1H, J=2.3 Hz), 7.45 (t, 1H, J=8.2 Hz), 7.27 (dd, 1H, J=2.3 and 8.2 Hz), 7.17 (d, 1H, J=3.5 Hz), 6.58 (d, 1H, J=3.5 Hz), 5.13 (s, 2H), 3.90 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resultant white solid was filtered
  3. washwashed with water and air
  4. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-3c5b8c562bf8420d839ba18c1bd1c9f2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822685B2

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