N,N,N',N'-Tetramethylmethanediamine → 5-((Dimethylamino)methyl)-2-furanmethanol

HRID 67879

Reaktionsgleichung

Reaktionsgleichung von HRID 67879
[CH3:1][N:2]([CH2:4]N(C)C)[CH3:3].[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][OH:14]>C(O)(=O)C>[CH3:1][N:2]([CH2:4][C:12]1[O:8][C:9]([CH2:13][OH:14])=[CH:10][CH:11]=1)[CH3:3]

Komponenten

4

Edukt 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7361Furfuryl Alcohol

Produkt 1

HCID 849065-((Dimethylamino)methyl)-2-furanmethanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of bis(dimethylamino)methane (112 g, 1.1 mol) in acetic acid (200 ml) was added dropwise with cooling (10° C.) to a stirred solution of 2-furanmethanol (98 g, 1.0 mol) in acetic acid (1000 ml). The mixture was stirred at room temperature for 18 hours and acetic acid was removed at 60° C. under reduced pressure. Ice (200 g) was added to the residue which was made basic with 40% aqueous sodium hydroxide (with external cooling). The mixture was extracted with ethyl acetate and the extracts were evaporated and distilled to give 5-dimethylaminomethyl-2-furanmethanol (145 g, 94%) b.p. 92°-96° C./0.2 0.5 mmHg.

Aufarbeitung

  1. customacetic acid was removed at 60° C. under reduced pressure
  2. additionIce (200 g) was added to the residue which
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe extracts were evaporated
  5. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-06afed7af5584767adb5809322c8679e
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04347191

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