Phenol → HCID 18541442, compound

HRID 411754Notes

Reaction equation

HRID 411754 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-79e64217892746c19b27767da2ebe432
Source dataset
uspto-grants-2003_05
Patent number
US06559185B2

Reaction notes

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