Phthalaldehyde → 6,13-Pentacenequinone

HRID 2251623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251623
[C:1]1(=[O:8])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH:9]1[CH:14]=[C:13]([CH:15]=O)[C:12]([CH:17]=O)=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)C>[CH:11]1[C:12]2[C:13](=[CH:15][C:6]3[C:1](=[O:8])[C:2]4[C:3]([C:4](=[O:7])[C:5]=3[CH:17]=2)=[CH:15][C:13]2[C:12](=[CH:11][CH:10]=[CH:9][CH:14]=2)[CH:17]=4)[CH:14]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 4807PhthalaldehydeHCID 125111,4-CyclohexanedioneHCID 14798Sodium Hydroxide

Produkt 1

HCID 764156,13-Pentacenequinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
47 °C

Versuchsvorschrift

A solution of 62.7 grams (0.559 mmoles, 1.0 equivalents) of cyclohexan-1,4-dione and 150 grams of o-phthalaldehyde (1.12 mmoles, 2.0 equivalents) in 2000 mL of ethanol was heat to 28° C. To this solution was added 220 mL of a 1M aqueous solution of sodium hydroxide. The reaction temperature increased to 47° C. during the addition. The mixture was then heated at 40° C. for 4 hours. The mixture was cooled and a yellow solid precipitate was collected. The solid was stirred in 2000 mL of N,N-dimethylformamide and heated to 50° C. for 2 hours. The mixture was cooled to room temperature (i.e., 20° C. to 25° C.) and the yellow solid was collected and washed with N,N-dimethylformamide, then with acetone and dried to give 108.3 grams (62 mole percent yield) of a bright yellow solid.

Aufarbeitung

  1. temperatureThe mixture was then heated at 40° C. for 4 hours
  2. temperatureThe mixture was cooled
  3. customa yellow solid precipitate was collected
  4. temperatureheated to 50° C. for 2 hours
  5. temperatureThe mixture was cooled to room temperature (i.e., 20° C. to 25° C.)
  6. customthe yellow solid was collected
  7. washwashed with N,N-dimethylformamide
  8. dry with materialwith acetone and dried
  9. customto give
  10. custom108.3 grams (62 mole percent yield) of a bright yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-130ce651217345bdab02fa2a67ca42f8
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319153B2

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