Phenol → Dimethyl phenoxyterephthalate

HRID 1803358Notes

Reaction equation

HRID 1803358 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-5a79a7897644472792d2da00155c2fa0
Source dataset
uspto-grants-2013_01
Patent number
US08350041B2

Reaction notes

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