Furfuryl Alcohol → N-(2-Furylmethoxy)phthalimide

HRID 918589

Reaktionsgleichung

Reaktionsgleichung von HRID 918589
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[O:22][CH:23]=[CH:24][CH:25]=1.C(O)C1OC=CC=1>O.CS(C)=O>[CH2:20]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:21]1[O:22][CH:23]=[CH:24][CH:25]=1

Komponenten

7

Edukt 4

HCID 7361Furfuryl AlcoholHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 2195202-(Chloromethyl)furan

Produkt 1

HCID 19975015N-(2-Furylmethoxy)phthalimideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred mixture of N-hydroxyphthalimide (41 g.), anhydrous potassium carbonate (26.4 g.) and dry dimethyl sulphoxide (400 ml.) was added 2-chloromethylfuran (freshly prepared, but undistilled, from 46.2 g. furfuryl alcohol according to the method of W. R. Kirner JACS, 1928, 50, 1955). The mixture was stirred for 18 hr., then poured into water (1.5 l). The precipitated solid was filtered off, washed well with water, and recrystallised from ethanol to give N-furfuryloxyphthalimide (42.8 g., 70%), m.p. 145.3°-146.2° τ values (DMSO-d6) are 4.80 (CH2), 2.22, 3.30, 3.50 (furyl protons) 2.08 (phthalimide protons).

Aufarbeitung

  1. customfreshly prepared
  2. filtrationThe precipitated solid was filtered off
  3. washwashed well with water
  4. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a4bf2e55461246e394cbe10f8e6f6f46
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971778

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