3-Methyl-5-(trifluoromethyl)benzoic acid → (3-Methyl-5-(trifluoromethyl)phenyl)methanol
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of 3-methyl-5-(trifluoromethyl)benzoic acid (1 g, 4.90 mmol) in THF (5 ml) at −78° C. under nitrogen was added dropwise over 10 mins borane tetrahydrofuran complex 1M in THF (24.49 ml, 24.49 mmol). The reaction mixture was then allowed to warm to RT over 20 hours. On cooling in an ice/water bath the reaction mixture was quenched dropwise with MeOH (10 ml) and then 1M HCl until effervescence ceased. Water was added and the reaction mixture stirred at RT for 30 mins and the THF was removed under reduced pressure. EtOAc was added and the organic portion dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in Hexanes as eluent to afford the title product;