Phenol → Dimethyl phenoxyterephthalate

HRID 425298Notes

Reaction equation

HRID 425298 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-d563a2fcf3d54a9da4fe9d1bb19e51a7
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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