Methanol → [5-(Phenyloxy)-2-(trifluoromethyl)phenyl]methanol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).