Malonic Acid → Furylacrylic acid

HRID 273667

Reaktionsgleichung

Reaktionsgleichung von HRID 273667
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.C(=O)[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.O>N1C=CC=CC=1.C(O)C.C(OCC)C>[O:13]1[CH:9]=[CH:10][CH:11]=[C:12]1[CH:3]=[CH:2][C:1]([OH:7])=[O:6]

Komponenten

7

Edukt 3

HCID 867Malonic AcidHCID 962WaterHCID 7362Furfural

Produkt 1

HCID 10876Furylacrylic acidAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Malonic acid (104 g; 1 mole) was dissolved in a mixture of furfural (96 g; 1 mole), pyridine (72 ml) and ethanol (10 ml) and pumped through the CMR (15 ml/min; 165° C.; 1200 kPa). The product mixture was diluted with diethyl ether (200 ml) and washed with 5% aqueous sulphuric acid (4×200 ml) to remove most of the pyridine. The remaining solution was evaporated to dryness on a rotary evaporator and the resultant 2-furanacrylic acid (25 g; 18% yield) crystallised from water m. p. 141° C. The MS was in close agreement with spectrum in the MS library. For a convention preparation see ref.18.

Aufarbeitung

  1. custompumped through the CMR (15 ml/min; 165° C.; 1200 kPa)
  2. washwashed with 5% aqueous sulphuric acid (4×200 ml)
  3. customto remove most of the pyridine
  4. customThe remaining solution was evaporated to dryness on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-754941a70720496981da1d5a812e9111
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387397

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