Phenol → HCID 18541442, compound

HRID 1584671Notes

Reaction equation

HRID 1584671 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-2a6c4623263749bbb0ad525f876b3e88
Source dataset
uspto-grants-1999_08
Patent number
US05932765

Reaction notes

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