Methanol → [5-(Phenyloxy)-2-(trifluoromethyl)phenyl]methanol

HRID 1946400Notes

Reaction equation

HRID 1946400 reaction equation
[C:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:17]([F:20])([F:19])[F:18])=[C:12]([CH:16]=2)[C:13](O)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C1COCC1>[C:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:17]([F:18])([F:19])[F:20])=[C:12]([CH2:13][OH:14])[CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 595479725-(Phenyloxy)-2-(trifluoromethyl)benzoic acid

Product 1

HCID 66770967[5-(Phenyloxy)-2-(trifluoromethyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of crude 5-(phenyloxy)-2-(trifluoromethyl)benzoic acid (for a preparation see Intermediate 36)(0.519 g, 1.84 mmol) in dry THF (40 ml) under nitrogen was added 1.0 M borane-tetrahydrofuran complex (6 ml, 6.0 mmol, Aldrich) dropwise. The solution was stirred for 30 min then heated at gentle reflux for 21 h. To the solution at ambient temperature was added methanol (10 ml) dropwise and then heated at reflux for 30 min. The solvent was removed in vacuo and then water added to the residue. The mixture was diluted with 2 M hydrochloric acid and the mixture was extracted with chloroform. The organic extract was concentrated in vacuo to give [5-(phenyloxy)-2-(trifluoromethyl)phenyl]methanol as a colourless oil (0.494 g).

Workup

  1. additionwas added 1.0 M borane-tetrahydrofuran complex (6 ml, 6.0 mmol, Aldrich) dropwise
  2. temperaturethen heated
  3. temperatureat gentle reflux for 21 h
  4. temperatureheated
  5. temperatureat reflux for 30 min
  6. customThe solvent was removed in vacuo
  7. additionwater added to the residue
  8. additionThe mixture was diluted with 2 M hydrochloric acid
  9. extractionthe mixture was extracted with chloroform
  10. extractionThe organic extract
  11. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-74dd6bd4cd2c40db83ca182897e1ddbd
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

Loading…