Methanol → 4-(Hydroxymethyl)-3-(trifluoromethyl)phenol
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.CO>C1COCC1>[OH:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][C:4]=1[C:11]([F:12])([F:13])[F:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-hydroxy-2-(trifluoromethyl)benzoic acid (4.62 g, 22.4 mmol, Fluorochem) in THF (60 ml) at ambient temperature under nitrogen was added dropwise 1.0 M borane-tetrahydrofuran complex (48 ml, 48.0 mmol). The solution was heated to 80° C. for 2 h. To the solution at ambient temperature was added methanol dropwise (40 ml). The solution was heated to 80° C. for 30 min. The solvent was removed in vacuo and the residue dissolved in methanol (100 ml). The solvent was removed in vacuo to leave the title compound as a white solid (4.39 g);
Workup
- temperatureThe solution was heated to 80° C. for 30 min
- customThe solvent was removed in vacuo
- dissolutionthe residue dissolved in methanol (100 ml)
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-c106a1be46754785b678e20e3d2e422d
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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