2-(Trifluoromethoxy)benzoic acid → 2-(Trifluoromethoxy)benzyl alcohol
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:7]>C1COCC1>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][OH:7]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-trifluoromethoxybenzoic acid (1.0 g, 5.2 mmol) in THF (25 mL) at 0° C. was added borane-THF complex (15 mL of a 1.0 M solution in THF, 15 mmol). The solution was warmed to ambient temperature and stirred for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (75 mL) and saturated aqueous NaHCO3 (75 mL). The organic phase was dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 2-trifluoromethoxybenzyl alcohol as a colorless liquid (TLC Rf =0.2 (1:3 EtOAc-hexanes)).
Workup
- customThe solvent was removed under reduced pressure
- customthe residue was partitioned between EtOAc (75 mL) and saturated aqueous NaHCO3 (75 mL)
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-fac91f98ab55453b8511f4a30fccc032
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090805
Reaction notes
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