Reaction #1340564

ord-4f10b447486b4bbc9511d7093e3fdcc6

Reaction equation

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

Reactants

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

Reagents

None

Solvents

c1ccncc1
pyridine
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherat room temperature
  2. 2
    Temperatureat reflux for 45 min
  3. 3
    TemperatureAfter reflux for a further hour
  4. 4
    Temperaturethe reaction mixture is heated
  5. 5
    Temperatureto reflux for 2 h

Procedure

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).

Source

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