Phenol → Dimethyl phenoxyterephthalate

HRID 733067Notes

Reaction equation

HRID 733067 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1I.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 10796Cesium carbonateHCID 637114Dimethyl iodoterephthalate

Product 1

HCID 23436153Dimethyl phenoxyterephthalateYield 103.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Iodo-terephthalic acid dimethyl ester (10 g, 31 mmol), phenol (3.23 g, 34 mmol), tetrakis-acetonitrilecopper hexafluorophosphate (2.9 g, 7.8 mmol), and cesium carbonate (10.2 g, 31 mmol) were added to a 1 L 3-neck round bottom flask equipped with a mechanical stirrer, a reflux condenser and containing toluene (350 mL). The reaction was refluxed 5 h under nitrogen with stirring. After cooling, EtOAc (200 mL) was added and the mixture was filtered. The filtrate was concentrated to afford the crude title compound (9.2 g) that was used without purification.

Workup

  1. customequipped with a mechanical stirrer, a reflux condenser
  2. temperatureThe reaction was refluxed 5 h under nitrogen
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eeae8e7d22a54873a60323d2c0a8d2a6
Source dataset
uspto-grants-2009_09
Patent number
US07589103B2

Reaction notes

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