Reaktion #1340564

ord-4f10b447486b4bbc9511d7093e3fdcc6

Reaktionsgleichung

CC(=O)c1cccc2c3ccccc3c3ccccc3c12
acetyltriphenylene
[Na+].[OH-]
NaOH
CCO
EtOH
II
I2
II
I2
→
O=C(O)c1ccc2c3ccccc3c3ccccc3c2c1
2-triphenylenecarboxylic acid
CC(=O)c1cccc2c3ccccc3c3ccccc3c12
acetyltriphenylene

Edukte

CC(=O)c1cccc2c3ccccc3c3ccccc3c12
acetyltriphenylene
[Na+].[OH-]
NaOH
CCO
EtOH
—
product
II
I2
II
I2

Reagenzien

Keine

Lösungsmittel

c1ccncc1
pyridine
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeat room temperature
  2. 2
    Temperaturat reflux for 45 min
  3. 3
    TemperaturAfter reflux for a further hour
  4. 4
    Temperaturthe reaction mixture is heated
  5. 5
    Temperaturto reflux for 2 h

Vorschrift

The reaction product obtained in step a) is admixed with 2.2 equivalents of I2 (based on the crude yield of acetyltriphenylene) in pyridine solvent at room temperature. Thereafter, the mixture is kept at reflux for 45 min, and then a further portion of I2 (1.0 equivalent) is added. After reflux for a further hour, NaOH, EtOH and water are added and the reaction mixture is heated to reflux for 2 h. 2-triphenylenecarboxylic acid is obtained in 76% yield (based on crude yield of acetyltriphenylene, or 74% based on triphenylene).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455112B2uspto-grants-2013_06