4-Nitro-o-toluic acid → (2-Methyl-4-nitrophenyl)methanol
Reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5]>C1COCC1.CO>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-methyl-4-nitrobenzoic acid (5 g, 27.6 mmol, Aldrich) in THF) (95 ml) was added dropwise 1.0 M borane-tetrahydrofuran complex (55 ml, 55.0 mmol, Aldrich) at ambient temperature under nitrogen. The resulting red solution was heated to 80° C. for 2 h. To the solution at ambient temperature was added methanol (30 ml) and then heated to 80° C. for 30 min. The solvent was evaporated in vacuo to leave a yellow oil. The residue was dissolved in methanol (80 ml) and the solvent evaporated in vacuo to leave (2-methyl-4-nitrophenyl)methanol as a yellow solid (4.73 g).
Workup
- temperatureheated to 80° C. for 30 min
- customThe solvent was evaporated in vacuo
- customto leave a yellow oil
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-69eef8c823434e7eab2fc1205ed4ff8b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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