Ethanol → Triphenylene-2-carboxylic acid

HRID 1253382Notes

Reaction equation

HRID 1253382 reaction equation
II.[C:3]([C:6]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[OH-:24].[Na+].[CH3:26][CH2:27][OH:28]>N1C=CC=CC=1.O>[CH:12]1[C:11]2[C:10]3[C:23](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][C:26]=1[C:27]([OH:24])=[O:28].[C:3]([C:6]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4]

Participants

8

Reactant 4

HCID 702EthanolHCID 807Iodine2×HCID 14798Sodium HydroxideHCID 86641842Acetyltriphenylene

Product 2

HCID 13802081Triphenylene-2-carboxylic acidHCID 86641842Acetyltriphenylene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

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).

Workup

  1. customat room temperature
  2. temperatureat reflux for 45 min
  3. temperatureAfter reflux for a further hour
  4. temperaturethe reaction mixture is heated
  5. temperatureto reflux for 2 h

Sources & evidence

ORD record
ord-4f10b447486b4bbc9511d7093e3fdcc6
Source dataset
uspto-grants-2013_06
Patent number
US08455112B2

Reaction notes

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