Acetic Acid → 2,9-Dimethylpentacene

HRID 488950

Reaktionsgleichung

Reaktionsgleichung von HRID 488950
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:20]([C:21](=O)[C:22]=2[CH:23]=1)=[CH:19][C:18]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=2)[C:10](=O)[C:9]=1[CH:8]=3.CO.C(O)(=O)C.Cl>COCCOCCOC.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=4)[CH:19]=3)[CH:23]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 114505987,14-Dihydro-3,10-dimethylpentacene-5,12-dione

Produkt 1

HCID 114609502,9-Dimethylpentacene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 24.6 grams of 7,14-dihydro-3,10-dimethylpentacene-5,12-dione in 250 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 10 minutes. To this was added in small portions 16.5 grams of sodium borohydride and stirring was continued at room temperature overnight. To the resulting reaction mixture was added slowly over 30 minutes 155 mL of methanol with the temperature maintained below 0° C. The mixture was stirred for 1.5 hours at room temperature. To the mixture was added slowly 360 mL of glacial acetic acid over 10 minutes. The resulting mixture was heated to 60° C. for 1.5 hours. To the mixture was added 100 mL of concentrated hydrochloric acid. The resulting mixture was heated for one hour and cooled to room temperature. To the mixture was added 250 mL of water and stirring was continued for five minutes. The resulting solid was collected by filtration and washed sequentially with 3 L of water, and 1 L of acetone, 1 L of tetrahydrofuran, and 1 L of acetone and dried to give 2,9-dimethylpentacene.

Aufarbeitung

  1. customflushed with nitrogen for 10 minutes
  2. additionTo this was added in small portions 16.5 grams of sodium borohydride
  3. stirringstirring
  4. customTo the resulting reaction mixture
  5. temperaturemaintained below 0° C
  6. stirringThe mixture was stirred for 1.5 hours at room temperature
  7. temperatureThe resulting mixture was heated for one hour
  8. temperaturecooled to room temperature
  9. stirringstirring
  10. waitwas continued for five minutes
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed sequentially with 3 L of water, and 1 L of acetone, 1 L of tetrahydrofuran, and 1 L of acetone
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5baa06ca0ba3459d9e04cedf7e8f1c44
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974877B2

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