Phenol → HCID 18541442, compound

HRID 1637905Notes

Reaction equation

HRID 1637905 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=O.S(Cl)(Cl)=O.CN(C)[CH:21]=[O:22].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]1[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=1[C:24]([O:22][C:21]1[CH:11]=[CH:12][CH:4]=[CH:5][CH:6]=1)=[O:30]

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27772232-(Trifluoromethoxy)benzoic acid

Product 1

HCID 18541442HCID 18541442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture composed of 10 g (48.5 mmol) of 2-(trifluoromethoxy)benzoic acid, 50 ml of thionyl chloride and a drop of dimethylformamide is heated under reflux for 1.5 hours. After cooling and concentrating the reaction mixture under vacuum, a residue is obtained which is stirred for 2 hours at 100° C. in the presence of 4.75 g (50 mmol) of phenol. After cooling, the reaction medium is taken up in dichloromethane, washed with a saturated NaHCO3 solution and then with water, dried over Na2SO4 and concentrated.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. temperatureAfter cooling
  3. concentrationconcentrating the reaction mixture under vacuum
  4. customa residue is obtained which
  5. temperatureAfter cooling
  6. washwashed with a saturated NaHCO3 solution
  7. dry with materialwith water, dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-58e447a2d6704be1ba784c7c4dcb9b01
Source dataset
uspto-grants-2000_03
Patent number
US06043281

Reaction notes

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