Hydrochloric Acid → Azulene

HRID 2287488

Reaktionsgleichung

Reaktionsgleichung von HRID 2287488
[C:1]1(C=O)[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:3](C=O)[CH:2]=1.S([O-])([O-])(=O)=O.[Mg+2].Cl.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 109761521,3-Azulenedicarboxaldehyde

Produkt 1

HCID 9231AzuleneAusbeute 225,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

1,3-Azulenedicarboxaldehyde (600 mg) is dissolved in 6.5 ml of pyridine. Magnesium sulfate (1200 mg) and N-tert-butylhydroxylammne hydrochloride (1638 mg,) is added to the solution,. The mixture is heated wit stirring to 95° C. under nitrogen and is stirred for 13 hours. Upon cooling to rt, the reaction mixture is poured into a separator flinnel containing 60 ml of CHCl3 and 60 ml of sat aq. NaHCO3. The aqueous layer is separated and washed with three 30 ml portions of CHCl3. The combined organc layers are dried over anhydrous MgSO4, filtered, and evaporated to give the bis-nitrone 34 (940 mg, 89% yield) as dark green crystals. Oxidation potential equals 0.72 V vs SCE. 1H NMR (CDCl3): 10.35 (s, 1H), 8.65 (d, 2H, J=10 Hz) 8.11 (s, 2H), 7.68 (t, 1H, J=10 Hz), 7.32 (t, 2H, J=10 Hz), 1.67 (s, 18H). 13C NMR (CDCl3): 139.9, 135.0, 134.2, 125.8, 125.6, 123.2, 120.5, 69.8, 28.4. IR (thin film): 3052, 2972, 1644, 1564, 1452, 1404, 1356, 1261, 1196, 1124, 1052, and 892 cm-1.

Aufarbeitung

  1. temperatureThe mixture is heated wit
  2. stirringis stirred for 13 hours
  3. temperatureUpon cooling to rt
  4. additionthe reaction mixture is poured into a separator flinnel
  5. customThe aqueous layer is separated
  6. washwashed with three 30 ml portions of CHCl3
  7. dry with materialThe combined organc layers are dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6cc3a8e7005c4c7cbdec9421686d4b7a
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06083988

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