Resorcinol → 9-(Carboxyethylidene)-3,6-dihydroxy-9H-xanthene

HRID 743951

Reaktionsgleichung

Reaktionsgleichung von HRID 743951
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]1(=O)[O:14][C:12](=[O:13])[CH2:11][CH2:10]1>>[C:12]([CH2:11][CH:10]=[C:9]1[C:6]2[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=2[O:2][C:1]2[C:8]1=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=2)([OH:14])=[O:13]

Komponenten

3

Edukt 2

HCID 5054ResorcinolHCID 7922Succinic anhydride

Produkt 1

HCID 199580049-(Carboxyethylidene)-3,6-dihydroxy-9H-xantheneAusbeute 88,4 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Resorcinol (33.0 g, 0.300 mol) and succinic anhydride (30.0 g, 0.300 mol) were placed in a round bottomed flask and purged with nitrogen. Methanesulfonic acid (150 mL) was added and the solution was stirred at 65° C. for 2 hours under an atmosphere of nitrogen. The reaction mixture was added dropwise to rapidly stirred, ice-cooled water (1 L) with simultaneous addition of 50% aqueous sodium hydroxide to maintain pH 2.5 +/0.5. The product which appeared as a granular precipitate was collected by filtration and rinsed with water (3×100 mL) then acetone (3×100 mL). The product was air-dried then vacuum-dried (vacuum oven) at 110° C. for 18 hours to afford a dark red powder (37.7 g, 88%).

Aufarbeitung

  1. custompurged with nitrogen
  2. additionMethanesulfonic acid (150 mL) was added
  3. additionThe reaction mixture was added dropwise
  4. stirringto rapidly stirred
  5. temperatureice-cooled water (1 L)
  6. additionwith simultaneous addition of 50% aqueous sodium hydroxide
  7. temperatureto maintain pH 2.5 +/0.5
  8. filtrationwas collected by filtration
  9. washrinsed with water (3×100 mL)
  10. customThe product was air-dried
  11. customthen vacuum-dried (vacuum oven) at 110° C. for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-cb49af7a587a4765b1d1c43e0838b79f
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05558991

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